Methyl Thioglycolate → 2-Chloro-4-fluoro-5-nitrothiobenzoic acid (methoxycarbonylmethyl) ester

HRID 1033214Notes

Reaction equation

HRID 1033214 reaction equation
ClC1C(C([CH2:10][C:11]([O:13][CH3:14])=[O:12])=S)=CC(N=C2N3N(CCCC3)C(=O)S2)=C(F)C=1.[Cl:27][C:28]1[CH:36]=[C:35]([F:37])[C:34]([N+:38]([O-:40])=[O:39])=[CH:33][C:29]=1[C:30](Cl)=[O:31].COC(=O)C[SH:45]>C(OCC)(=O)C>[CH3:14][O:13][C:11]([CH2:10][O:31][C:30](=[S:45])[C:29]1[CH:33]=[C:34]([N+:38]([O-:40])=[O:39])[C:35]([F:37])=[CH:36][C:28]=1[Cl:27])=[O:12]

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 151243842-Chloro-4-fluoro-5-nitrobenzoyl chlorideHCID 542425799-[4-Chloro-2-fluoro-5-(methoxycarbonylmethylthiocarbonyl)-phenylimino]-8-thia-1,6-diazabicyclo[4.3.0]nonan-7-one

Product 1

HCID 540569242-Chloro-4-fluoro-5-nitrothiobenzoic acid (methoxycarbonylmethyl) ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The preparation of 9-[4-chloro-2-fluoro-5-(methoxycarbonylmethylthiocarbonyl)-phenylimino]-8-thia-1,6-diazabicyclo[4.3.0]nonan-7-one is given by way of example: ##STR22## 48 g of 2-chloro-4-fluoro-5-nitrobenzoic acid chloride are added dropwise, with stirring, at room temperature to a solution of 20 ml of thioglycolic acid methyl ester in 100 ml of ethyl acetate. The batch is stirred for 18 hours and then the solvent is evaporated off in vacuo to yield 19 g of 2-chloro-4-fluoro-5-nitrothiobenzoic acid (methoxycarbonylmethyl) ester in the form of an oil having nD23 : 1.5709.

Workup

  1. customthe solvent is evaporated off in vacuo

Sources & evidence

ORD record
ord-1d7d8caf462e4bab92a4806ab67409e8
Source dataset
uspto-grants-1994_05
Patent number
US05310722

Reaction notes

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