Hydrogen Sulfide → 3-Amino-2-cyano-3-isopropoxy-2-propenethioamide

HRID 1439334Notes

Reaction equation

HRID 1439334 reaction equation
[NH2:1][C:2]([O:8][CH:9]([CH3:11])[CH3:10])=[C:3]([C:6]#[N:7])[C:4]#[N:5].[SH2:12].C(N(CC)CC)C>N1C=CC=CC=1>[NH2:1][C:2]([O:8][CH:9]([CH3:11])[CH3:10])=[C:3]([C:4]#[N:5])[C:6](=[S:12])[NH2:7]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 213968063-Amino-2-cyano-3-isopropoxy-2-propenenitrile

Product 1

HCID 859269193-Amino-2-cyano-3-isopropoxy-2-propenethioamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In the manner of Example V, part B, 117.6 g of 3-amino-2-cyano-3-isopropoxy-2-propenenitrile were allowed to react with excess hydrogen sulfide gas in a solution of 157.4 g of triethylamine and 250 ml of pyridine. The volatile materials were removed under reduced pressure and water was added to the residue. The yellow precipitate was collected and dried. The dried solid was recrystallized from isopropanol to yield 123 g of 3-amino-2-cyano-3-isopropoxy-2-propenethioamide, mp 170° (decomposes). The ir and nmr spectra were consistent with the assigned structure.

Workup

  1. customThe volatile materials were removed under reduced pressure and water
  2. additionwas added to the residue
  3. customThe yellow precipitate was collected
  4. customdried
  5. customThe dried solid was recrystallized from isopropanol

Sources & evidence

ORD record
ord-6792ad7d38ab4525b78fca338af1d5a1
Source dataset
uspto-grants-1977_11
Patent number
US04059433

Reaction notes

Loading…