Hydrogen Sulfide → HCID 86742186, compound

HRID 1253028Notes

Reaction equation

HRID 1253028 reaction equation
C(C[C:4]1[NH:5][CH:6]=[CH:7][CH: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:5][CH:6]=[CH:7][CH:8]=1)(=[S:16])[CH3:10]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 13067931(1H-Pyrrol-2-yl)-acetonitrile

Product 1

HCID 86742186HCID 86742186, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

2-Cyanomethylpyrrole (2.7 g, 25 mmole) was dissolved in 25 ml of dry pyridine. The solution was cooled to 0° C. in a medium pressure glass tube. Hydrogen sulfide was bubbled into the solution for 10 minutes followed by the addition of 1.5 equivalents of triethylamine (5.4 ml). The tube was sealed and heated in a steam bath for 5 hours. After cooling, the tube was opened, venting the excess hydrogen sulfide gas, and the excess pyridine was removed under reduced pressure. Recrystallization from ethyl acetate/hexane yielded 2.2 gm of 2-thioacetamidopyrrole. m.p. 93°-94° C.

Workup

  1. customHydrogen sulfide was bubbled into the solution for 10 minutes
  2. customThe tube was sealed
  3. temperatureheated in a steam bath for 5 hours
  4. temperatureAfter cooling
  5. customthe excess pyridine was removed under reduced pressure
  6. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-00e809b073f245a095b0fd91e8ca7d0c
Source dataset
uspto-grants-1988_05
Patent number
US04746669

Reaction notes

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