Triethylamine → 1-(3-Benzoylthio-2-methylpropanoyl)-3,3-dimethylindoline-2-carboxylic acid

HRID 745612Notes

Reaction equation

HRID 745612 reaction equation
Cl.[CH3:2][C:3]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]1[C:12]([OH:14])=[O:13].C(N(CC)CC)C.[C:23]([S:31][CH2:32][CH:33]([CH3:37])[C:34](Cl)=[O:35])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[C:23]([S:31][CH2:32][CH:33]([CH3:37])[C:34]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([CH3:15])([CH3:2])[CH:4]1[C:12]([OH:14])=[O:13])=[O:35])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12878433(1)-S-(3-Chloro-2-methyl-3-oxopropyl) benzenecarbothioateHCID 704701543,3-dimethyl-2,3-dihydro-1H-indole-2-carboxylic acid hydrochloride

Product 1

HCID 233138471-(3-Benzoylthio-2-methylpropanoyl)-3,3-dimethylindoline-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the suspension of 1.0 g of 3,3-dimethylindoline-2-carboxylic acid hydrochloride in 25 ml of methylene chloride, 1.33 g of triethylamine are added and the resulting solution cooled to -10°. The solution of 1.065 g of 3-benzoylthio-2-methylpropanoyl chloride in 5 ml of methylene chloride is added dropwise and the mixture stirred at -5° for 1 hour, and then at room temperature for 2 hours. It is evaporated, 10 ml of 3N hydrochloric acid are added to the residue and the mixture is extracted with methylene chloride. The extract is dried and evaporated, to give the 1-(3-benzoylthio-2-methylpropanoyl)-3,3-dimethylindoline-2-carboxylic acid.

Workup

  1. additionare added
  2. temperaturethe resulting solution cooled to -10°
  3. waitat room temperature for 2 hours
  4. customIt is evaporated
  5. addition10 ml of 3N hydrochloric acid are added to the residue
  6. extractionthe mixture is extracted with methylene chloride
  7. customThe extract is dried
  8. customevaporated

Sources & evidence

ORD record
ord-a1796d3f5e99487dabf1310fc99350ba
Source dataset
uspto-grants-1986_07
Patent number
US04599357

Reaction notes

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