Dichloromethane → 1-(3-(Benzoylthio)-2-methylpropanoyl)-2-indolinecarboxylic acid

HRID 745609Notes

Reaction equation

HRID 745609 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[C:11]([OH:13])=[O:12].C(Cl)Cl.[C:17]([S:25][CH2:26][CH:27]([CH3:31])[C:28](Cl)=[O:29])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(N(CC)CC)C>[C:17]([S:25][CH2:26][CH:27]([CH3:31])[C:28]([N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[C:11]([OH:13])=[O:12])=[O:29])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 12878433(1)-S-(3-Chloro-2-methyl-3-oxopropyl) benzenecarbothioateHCID 67437533Indoline-2-carboxylic acid hydrochloride

Product 1

HCID 4943231-(3-(Benzoylthio)-2-methylpropanoyl)-2-indolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To the mixture of 5.0 g of indoline-2-carboxylic acid hydrochloride and 50 ml of methylene chloride are added 7.9 g of triethylamine, and after 5 minutes 6.1 g of 3-benzoylthio-2-methylpropanoyl chloride during 3 minutes. After stirring the mixture at room temperature for 2 hours, it is extracted thrice with 50 ml of saturated aqueous sodium bicarbonate. The combined aqueous solutions are adjusted to pH=1 with 4N hydrochloric acid and reextracted thrice with 50 ml of methylene chloride. The combined extracts are dried and evaporated, to yield the 1-(3-benzoylthio-2-methylpropanoyl)-indoline-2-carboxylic acid.

Workup

  1. extractionit is extracted thrice with 50 ml of saturated aqueous sodium bicarbonate
  2. customThe combined extracts are dried
  3. customevaporated

Sources & evidence

ORD record
ord-1ac35ae9687440148a1c29ef257f62a7
Source dataset
uspto-grants-1986_07
Patent number
US04599357

Reaction notes

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