Hydrochloric Acid → 2-(4-Hydroxyiminopiperidin-1-yl)-2-iminoethylmercaptan hydrochloride

HRID 622414Notes

Reaction equation

HRID 622414 reaction equation
P(=[S:5])([O-])([O-])[O-].[Na+].[Na+].[Na+].Cl.[OH:10][N:11]=[C:12]1[CH2:17][CH2:16][N:15]([C:18](=[NH:21])[CH2:19][Cl:20])[CH2:14][CH2:13]1.Cl>O>[ClH:20].[OH:10][N:11]=[C:12]1[CH2:17][CH2:16][N:15]([C:18](=[NH:21])[CH2:19][SH:5])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9877537Trisodium thiophosphateHCID 212929432-(4-Hydroxyiminopiperidin-1-yl)-2-iminoethylchloride hydrochloride

Product 1

HCID 212929702-(4-Hydroxyiminopiperidin-1-yl)-2-iminoethylmercaptan hydrochlorideYield 86.6%

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-(4-hydroxyiminopiperidin-1-yl)-2-iminoethylchloride hydrochloride in 12 ml of water, 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 reaction mixture was concentrated under reduced pressure, the concentrate was mixed with 9.8 ml of methanol, and insolubles were filtered off. The filtrate was concentrated under reduced pressure, ether was added to the concentrate, and the crystals which separated out were collected by filtration and washed with ether, giving 1.8 g of 2-(4-hydroxyiminopiperidin-1-yl)-2-iminoethylmercaptan hydrochloride.

Workup

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

Sources & evidence

ORD record
ord-873eb88772094d1ab413f6d2bf73f9c7
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

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