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

HRID 622431Notes

Reaction equation

HRID 622431 reaction equation
P(=[S:5])([O-])([O-])[O-].[Na+].[Na+].[Na+].Cl.[O:10]=[C:11]1[NH:16][CH2:15][CH2:14][N:13]([C:17](=[NH:20])[CH2:18][Cl:19])[CH2:12]1.Cl>O>[ClH:19].[O:10]=[C:11]1[NH:16][CH2:15][CH2:14][N:13]([C:17](=[NH:20])[CH2:18][SH:5])[CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9877537Trisodium thiophosphateHCID 212929452-(3-Oxopiperazin-1-yl)-2-iminoethylchloride hydrochloride

Product 1

HCID 212929952-(3-Oxopiperazin-1-yl)-2-iminoethylmercaptan hydrochlorideYield 45.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.0 g of trisodium phosphorothioate were added to a solution of 14.3 g of 2-(3-oxopiperazin-1-yl)-2-iminoethylchloride hydrochloride in 80 ml of water, kept cooled in ice-water, and the mixture was stirred at room temperature for one hour. After adding 66.5 ml of 1N hydrochloric acid, the mixture was heated to 50° C. for 30 minutes, and the solvent was then distilled off under reduced pressure. The concentrate was mixed with 200 ml of methanol, insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The concentrate was crystallized by adding ether, and the crystals were collected by filtration and washed with ether, giving 6.4 g of 2-(3-oxopiperazin-1-yl)-2-iminoethylmercaptan hydrochloride.

Workup

  1. temperaturethe mixture was heated to 50° C. for 30 minutes
  2. distillationthe solvent was then distilled off under reduced pressure
  3. additionThe concentrate was mixed with 200 ml of methanol, insolubles
  4. filtrationwere filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe concentrate was crystallized
  7. additionby adding ether
  8. filtrationthe crystals were collected by filtration
  9. washwashed with ether

Sources & evidence

ORD record
ord-47ed0d6dc96f440f85bd36c03ab62b4f
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

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