Hydrogen Sulfide → HCID 54241450, compound

HRID 1253032Notes

Reaction equation

HRID 1253032 reaction equation
C(C[C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)#N.[CH2:9]([N:11](CC)CC)[CH3:10].[SH2:16]>N1C=CC=CC=1>[C:9]([NH:11][C:4]1[NH:8][CH:7]=[CH:6][N:5]=1)(=[S:16])[CH3:10]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 14207546(1H-Imidazol-2-yl)acetonitrile

Product 1

HCID 54241450HCID 54241450, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Cyanomethylimidazole (0.83 g, 7.7 mmole) in 20 ml of dry pyridine was added to a medium pressure glass tube and was bubbled with hydrogen sulfide gas for 10 minutes. Then 1.5 equivalents of triethylamine (1.1 ml) was added. The tube was sealed and heated in a steam bath for 4 hours. The pressure tube was cooled and the excess hydrogen sulfide vented. Pyridine was removed under reduced pressure. Recrystallization from ethyl acetate-hexane afforded 0.42 gm of 2-thioacetamidoimidazole. m.p. 174° C. (decomposition).

Workup

  1. customwas bubbled with hydrogen sulfide gas for 10 minutes
  2. customThe tube was sealed
  3. temperatureheated in a steam bath for 4 hours
  4. temperatureThe pressure tube was cooled
  5. customPyridine was removed under reduced pressure
  6. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ee47cfd4272b49c189c565c5e65f639a
Source dataset
uspto-grants-1988_05
Patent number
US04746669

Reaction notes

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