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

HRID 622417Notes

Reaction equation

HRID 622417 reaction equation
P(=[S:5])([O-])([O-])[O-].[Na+].[Na+].[Na+].Cl.[CH3:10][O:11][N:12]=[C:13]1[CH2:18][CH2:17][N:16]([C:19](=[NH:22])[CH2:20][Cl:21])[CH2:15][CH2:14]1.Cl>O>[ClH:21].[CH3:10][O:11][N:12]=[C:13]1[CH2:18][CH2:17][N:16]([C:19](=[NH:22])[CH2:20][SH:5])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9877537Trisodium thiophosphateHCID 212929772-(4-Methoxyiminopiperidin-1-yl)-2-iminoethylchloride hydrochloride

Product 1

HCID 212930122-(4-Methoxyiminopiperidin-1-yl)-2-iminoethylmercaptan hydrochlorideYield 62.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.03 g of trisodium phosphorothioate was added to a solution of 1.472 g of 2-(4-methoxyiminopiperidin-1-yl)-2-iminoethylchloride hydrochloride in 7 ml of water, kept cooled in ice-water, and the mixture was stirred at room temperature for about one hour. 5.7 ml of 1N hydrochloric acid were then added, followed by heating at 65° C. for 30 minutes. The resulting solution was concentrated under reduced pressure, mixed with ether, filtered to remove insolubles, and the filtrate concentrated under reduced pressure. The concentrate was mixed with isopropanol, and the crystals which separated out were collected by filtration and reprecipitated from a mixture of ethanol and ether, giving 850 mg of 2-(4-methoxyiminopiperidin-1-yl)-2-iminoethylmercaptan hydrochloride.

Workup

  1. temperatureby heating at 65° C. for 30 minutes
  2. concentrationThe resulting solution was concentrated under reduced pressure
  3. additionmixed with ether
  4. filtrationfiltered
  5. customto remove insolubles
  6. concentrationthe filtrate concentrated under reduced pressure
  7. additionThe concentrate was mixed with isopropanol
  8. customthe crystals which separated out
  9. filtrationwere collected by filtration
  10. customreprecipitated from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-d19fe18d05e74ac2923704992fba1e1d
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

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