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

HRID 622423Notes

Reaction equation

HRID 622423 reaction equation
P(=[S:5])([O-])([O-])[O-].[Na+].[Na+].[Na+].Cl.[OH:10][N:11]=[C:12]1[CH2:16][CH2:15][N:14]([C:17](=[NH:20])[CH2:18][Cl:19])[CH2:13]1.Cl>O>[ClH:19].[OH:10][N:11]=[C:12]1[CH2:16][CH2:15][N:14]([C:17](=[NH:20])[CH2:18][SH:5])[CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9877537Trisodium thiophosphateHCID 867424302-(3-Hydroxyiminopyrrolidin-1-yl)-2-iminoethylchloride hydrochloride

Product 1

HCID 867424332-(3-Hydroxyiminopyrrolidin-1-yl)-2-iminoethylmercaptan hydrochlorideYield 64.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

945 mg of trisodium phosphorothioate were added to a solution of 1.05 g of 2-(3-hydroxyiminopyrrolidin-1-yl)-2-iminoethylchloride hydrochloride in 6.4 ml of water, cooled with ice-water, and the mixture was stirred at room temperature for about one hour. 5.2 ml of 1N hydrochloric acid were added, and the mixture was heated at 65° C. for 30 minutes and then concentrated under reduced pressure. The concentrate was mixed with 5.2 ml of methanol, insolubles were filtered off, and the filtrate was concentrated under reduced pressure. Anhydrous ether was added to the concentrate, and the precipitated crystals were collected by filtration and washed with ether, giving 670 mg of 2-(3-hydroxyiminopyrrolidin-1-yl)-2-iminoethylmercaptan hydrochloride.

Workup

  1. temperaturethe mixture was heated at 65° C. for 30 minutes
  2. concentrationconcentrated under reduced pressure
  3. additionThe concentrate was mixed with 5.2 ml of methanol, insolubles
  4. filtrationwere filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionAnhydrous ether was added to the concentrate
  7. filtrationthe precipitated crystals were collected by filtration
  8. washwashed with ether

Sources & evidence

ORD record
ord-02014e8f7cfa476889b69de7191d4aee
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

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