Hydrochloric Acid → 2-(3-Methoxyiminopyrrolidin-1-yl)-2-iminoethylmercaptan hydrochloride

HRID 622420Notes

Reaction equation

HRID 622420 reaction equation
P(=[S:5])([O-])([O-])[O-].[Na+].[Na+].[Na+].Cl.[CH3:10][O:11][N:12]=[C:13]1[CH2:17][CH2:16][N:15]([C:18](=[NH:21])[CH2:19][Cl:20])[CH2:14]1.Cl>O>[ClH:20].[CH3:10][O:11][N:12]=[C:13]1[CH2:17][CH2:16][N:15]([C:18](=[NH:21])[CH2:19][SH:5])[CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9877537Trisodium thiophosphateHCID 867424272-(3-Methoxyiminopyrrolidin-1-yl)-2-iminoethylchloride hydrochloride

Product 1

HCID 867424292-(3-Methoxyiminopyrrolidin-1-yl)-2-iminoethylmercaptan hydrochlorideYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.77 g of trisodium phosphorothioate were added to an ice-cooled solution of 2.1 g of 2-(3-methoxyiminopyrrolidin-1-yl)-2-iminoethylchloride hydrochloride in 12 ml of water, and the mixture was stirred at room temperature for about one hour. 9.8 ml of 1N hydrochloric acid were then added, and the mixture was heated at 65° C. for 30 minutes. The resulting solution was concentrated under reduced pressure, the concentrate was mixed with 9.8 ml of isopropanol, insolubles were filtered off, and the filtrate was concentrated under reduced pressure. Ether was added to the concentrate, and the crystals which separated out were collected by filtration and reprecipitated from a mixture of ethanol and ether, giving 1.6 g of 2-(3-methoxyiminopyrrolidin-1-yl)-2-iminoethylmercaptan hydrochloride.

Workup

  1. temperaturethe mixture was heated at 65° C. for 30 minutes
  2. concentrationThe resulting solution was concentrated under reduced pressure
  3. additionthe concentrate was mixed with 9.8 ml of isopropanol, insolubles
  4. filtrationwere filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionEther was added to the concentrate
  7. customthe crystals which separated out
  8. filtrationwere collected by filtration
  9. customreprecipitated from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-561924d555e245bea9c6b81c156da4be
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

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