Prepn. of E-oxime ether(s) of phenyl-glyoxylic acid ester(s)

    公开(公告)号:DE4042282A1

    公开(公告)日:1992-07-02

    申请号:DE4042282

    申请日:1990-12-31

    Applicant: BASF AG

    Abstract: Prepn. of E-oxime-ethers of phenylglyoxylic acid esters of formula (I) comprises (a) reacting a phenol Xm-Ph-PH in a base in the presence of a solvent to give a phenolate; (b) mixing with a lactone of formula (III); (c) distilling off solvent and reacting the mixt. at 50-250 deg.C in the melt; (d) washing with water and acid to give a 2-phenoxymethylbenzoic acid of formula (IV); Q = OH); (e) treating with phosgene or SOCl2 to give the 2-phenoxymethylbenzoyl chloride (IV; Q = Cl); (f) reacting with alkali(ne earth)metal cyanide opt. in the presence of prussic acid; (g) treating the 2-phenoxymethylbenzoyl cyanide (IV; Q = CN) with MeOH in the presence of acid to give (VIIb); (h) opt. splitting under acidic conditions to give (IV; Q = C(O)NHR) or (i) treating (IV; Q=R) with dimethyl sulphoxide in the presence of a base to give a beta ketosulphoxide (IV; Q = CH2SOCH3) and treating with a halogenating agent, and MeOH in acid to give (IV; Q = C(O)OMe); (k) reacting (IV; Q = C(O)OMe) and/or (VIIb) with O-methylhydroxylamine or its acid addn. salt to give (I). Q = R1CH2SOMe, OH, Cl, CN or C(O)NNR; X, Y = halo, 1-4C alkyl, 1-4C alkoxy or CF3; m = 0-4; n = 0-3; R = 1-4C alkyl.

    Prepn. of E-oxime ether(s) of phenyl-glyoxylic acid ester(s)

    公开(公告)号:DE4042280A1

    公开(公告)日:1992-07-02

    申请号:DE4042280

    申请日:1990-12-31

    Applicant: BASF AG

    Abstract: Prepn. of E-oxime-ethers of phenylglyoxylic acid esters of formula (I) comprises (a) reacting a phenol Xm-Ph-PH in a base in the presence of a solvent to give a phenolate; (b) mixing with a lactone of formula (III); (c) distilling off solvent and reacting the mixt. at 50-250 deg.C in the melt; (d) washing with water and acid to give a 2-phenoxymethylbenzoic acid of formula (IV); Q = OH); (e) treating with phosgene or SOCl2 to give the 2-phenoxymethylbenzoyl chloride (IV; Q = Cl); (f) reacting with alkali(ne earth)metal cyanide opt. in the presence of prussic acid; (g) treating the 2-phenoxymethylbenzoyl cyanide (IV; Q = CN) with MeOH in the presence of acid to give (VIIb); (h) opt. splitting under acidic conditions to give (IV; Q = C(O)NHR) or (i) treating (IV; Q=R) with dimethyl sulphoxide in the presence of a base to give a beta ketosulphoxide (IV; Q = CH2SOCH3) and treating with a halogenating agent, and MeOH in acid to give (IV; Q = C(O)OMe); (k) reacting (IV; Q = C(O)OMe) and/or (VIIb) with O-methylhydroxylamine or its acid addn. salt to give (I). Q = R1CH2SOMe, OH, Cl, CN or C(O)NNR; X, Y = halo, 1-4C alkyl, 1-4C alkoxy or CF3; m = 0-4; n = 0-3; R = 1-4C alkyl.

    96.
    发明专利
    未知

    公开(公告)号:AT248142T

    公开(公告)日:2003-09-15

    申请号:AT01115054

    申请日:2001-06-21

    Applicant: BASF AG

    Abstract: Hydrazonomethyl-salicylic acid (I) derivatives are new. The hydrazonomethyl-salicylic acid derivatives are compounds of formula (I). X = halo, NO2, CN, 1-4C alkyl, or 1-4C alkoxy; m = 0-3; A = OH, 1-4C alkoxy, NH2, NHCH3, or N(CH3)2; R = phenyl, naphthyl, 3-10C cycloalkyl, 5- or 6-membered heteroaryl or heterocyclyl containing 1-3 N and/or 1 O or S or 1 or 2 O and/or S (each optionally substituted with 1-3 Ra); Ra = CN, NO2, NH2, H2NCO-, H2NCS-, halo, OH, 1-6C alkyl or 1-6C alkoxy (each optionally substituted with halo), 1-6C alkylcarbonyl, 1-6C alkylsulfonyl, 1-6C alkylsulfoxyl, 3-6C cycloalkyl, 1-6C alkoxycarbonyl, 1-6C alkylthio, NH(1-6C alkyl), N(1-6C alkyl)2, 1-6C alkyl-NH-CO-, (1-6C alkyl)2N-CO-, 1-6C alkyl-NH-CS-, (1-6C alkyl)2N-CS-, 2-6C alkenyl, 2-6C alkenyloxy, phenyl, phenoxy, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, heteroaryl or heteroaryloxy, C(=NOR alpha )-OR beta , or OC(R alpha )2-C(R beta )=NOR beta , and cyclic groups are optionally substituted with 1-3 Rb; Rb = CN, NO2, NH2, H2NCO-, H2NCS-, halo, OH, 1-6C alkyl or 1-6C alkoxy (each optionally substituted with halo), 1-6C alkylcarbonyl, 1-6C alkylsulfonyl, 1-6C alkylsulfoxyl, 3-6C cycloalkyl, 1-6C alkoxycarbonyl, 1-6C alkylthio, NH(1-6C alkyl), N(1-6C alkyl)2, 1-6C alkyl-NH-CO-, (1-6C alkyl)2N-CO-, 1-6C alkyl-NH-CS-, (1-6C alkyl)2N-CS-, 2-6C alkenyl, 2-6C alkenyloxy, 3-6C cycloalkenyl, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, heteroaryl or heteroaryloxy, or C(=NOR alpha )-OR beta ; R alpha and R beta = H or 1-6C alkyl; R = H, CN, or 1-6C alkyl, 2-6C alkenyl, 2-6C alkynyl, 1-6C haloalkyl, 1-6C alkoxy or 1-6C alkylthio (each optionally substituted with 1 or more halo and/or 1-3 Rc); Rc = halo, CN, NO2, OH; 1-6C alkyl or 1-6C alkoxy (each optionally substituted with halo); 1-6C alkylcarbonyl, 3-6C cycloalkyl, 1-6C alkoxycarbonyl, 1-6C alkylthio, NH(1-6C alkyl), N(1-6C alkyl)2, 2-6C alkenyl, 3-6C alkenyloxy, 3-6C alkynyloxy, or 1-4C alkylenedioxy (optionally halogenated). An Independent claim is also included for the preparation of compounds (I).

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