Hydrogen Sulfide → 3-Amino-2-cyano-3-(dipropylamino)propenethioamide

HRID 616508Notes

Reaction equation

HRID 616508 reaction equation
[NH2:1][C:2]([N:8]([CH2:12][CH2:13][CH3:14])[CH2:9][CH2:10][CH3:11])=[C:3]([C:6]#[N:7])[C:4]#[N:5].C(N(CC)CC)C.[SH2:22]>N1C=CC=CC=1>[NH2:1][C:2]([N:8]([CH2:9][CH2:10][CH3:11])[CH2:12][CH2:13][CH3:14])=[C:3]([C:4]#[N:5])[C:6](=[S:22])[NH2:7]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 859420343-Amino-2-cyano-3-(dipropylamino)propenenitrile

Product 1

HCID 859420353-Amino-2-cyano-3-(dipropylamino)propenethioamideYield 29.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

An attempt at conversion by the method of Example IV, part D, was unsuccessful. Thus a mixture of 28 g of 3-amino-2-cyano-3-(dipropylamino)propenenitrile, 14.7 g of triethylamine and 100 ml of pyridine in a pressure bottle was cooled to -70° and 10 g of hydrogen sulfide were added. The bottle was capped and allowed to stand at ambient temperature during two days, then heated at 80° for about 16 hours. The mixture was concentrated under reduced pressure and the residue was dissolved in a minimum of toluene containing a trace of ethanol. The solid which separated on cooling was collected to obtain 9.6 g of 3-amino-2-cyano-3-(dipropylamino)propenethioamide, m.p. 141°-144°. The nmr spectrum was consistent with the assigned structure.

Workup

  1. temperaturewas cooled to -70°
  2. customThe bottle was capped
  3. temperatureheated at 80° for about 16 hours
  4. concentrationThe mixture was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in a minimum of toluene containing a trace of ethanol
  6. customThe solid which separated
  7. temperatureon cooling
  8. customwas collected

Sources & evidence

ORD record
ord-4e803c09bf624e8ba5e2e11fd4209699
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

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