Hydrogen Sulfide → HCID 85942030, compound

HRID 616503Notes

Reaction equation

HRID 616503 reaction equation
[NH2:1][C:2]([N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)=[C:3]([C:6]#[N:7])[C:4]#[N:5].C(N(CC)CC)C.[SH2:20]>N1C=CC=CC=1>[NH2:1][C:2]([N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)=[C:3]([C:4]#[N:5])[C:6](=[S:20])[NH2:7]

Participants

5

Reactant 3

HCID 402Hydrogen Sulfide2×HCID 8471TriethylamineHCID 85964870HCID 85964870, compound

Product 1

HCID 85942030HCID 85942030, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 93.3 g of 3-amino-2-cyano-3-(1-pyrrolidinyl)propenenitrile, 58.2 g of triethylamine and 400 ml of pyridine was heated at 60°-65° and hydrogen sulfide passed in for 21/2 hours. While continuing the addition of hydrogen sulfide, the temperature of the mixture was increased to 80°, where it was maintained for two and a half hours. The mixture stood for 64 hours at ambient temperature, then was heated at 90° for 21/2 hours. The mixture was concentrated under reduced pressure. The tan solid residue was stirred with 750 ml of ice-water, the cold slurry was filtered and the solid was washed with cold water. The washed solid was recrystallized from 1200 ml of ethanol to give 87.4 g (three crops) of 3-amino-2-cyano-3-(1-pyrrolidinyl)propenethioamide, m.p. 164°. The nmr spectrum was consistent with the assigned structure.

Workup

  1. temperaturewas heated at 60°-65°
  2. custom2 hours
  3. temperaturethe temperature of the mixture was increased to 80°
  4. temperaturewhere it was maintained for two and a half hours
  5. temperaturewas heated at 90° for 21/2 hours
  6. concentrationThe mixture was concentrated under reduced pressure
  7. filtrationthe cold slurry was filtered
  8. washthe solid was washed with cold water
  9. customThe washed solid was recrystallized from 1200 ml of ethanol

Sources & evidence

ORD record
ord-c068b2956394416783bf16976fc8f3f7
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

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