Hydrochloric Acid → HCID 23313838, compound

HRID 745606Notes

Reaction equation

HRID 745606 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][C:10]1([CH3:22])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]1[C:19]([OH:21])=[O:20].[C:23]([S:26][CH2:27][CH2:28][C:29](Cl)=[O:30])(=[O:25])[CH3:24].Cl>C(Cl)Cl>[C:23]([S:26][CH2:27][CH2:28][C:29]([N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH3:22])([CH3:9])[CH:11]1[C:19]([OH:21])=[O:20])=[O:30])(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 129431223-(Acetylsulfanyl)propanoyl chlorideHCID 704701543,3-dimethyl-2,3-dihydro-1H-indole-2-carboxylic acid hydrochloride

Product 1

HCID 23313838HCID 23313838, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.93 g of triethylamine are added to the suspension of 0.7 g of 3,3-dimethylindoline-2-carboxylic acid hydrochloride in 20 ml of methylene chloride and the resulting solution is cooled to -10°. The solution of 0.51 g of 3-acetylthiopropanoyl chloride in 5 ml of methylene chloride is added dropwise and the mixture stirred at -5° to -10° for 1 hour and at room temperature for 3 hours. It is cooled to 0° and treated with 10 ml of 3N hydrochloric acid. The organic layer is separated and the aqueous solution further extracted with methylene chloride. The combined methylene chloride solutions are dried and evaporated, to give the 1-(3-acetylthiopropanoyl)-3,3-dimethylindoline-2-carboxylic acid as a foam.

Workup

  1. temperaturethe resulting solution is cooled to -10°
  2. temperatureIt is cooled to 0°
  3. customThe organic layer is separated
  4. extractionthe aqueous solution further extracted with methylene chloride
  5. dry with materialThe combined methylene chloride solutions are dried
  6. customevaporated

Sources & evidence

ORD record
ord-fb23bb495720428daa47716788fc5e74
Source dataset
uspto-grants-1986_07
Patent number
US04599357

Reaction notes

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