Hydrogen Sulfide → HCID 13021420, compound

HRID 263326Notes

Reaction equation

HRID 263326 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]([C:19]([O:21][CH2:22][CH3:23])=[O:20])([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)[NH:6][C:7](=[O:9])[CH3:8])[CH3:2].C(N(CC)CC)C.[SH2:32]>N1C=CC=CC=1>[CH2:22]([O:21][C:19](=[O:20])[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:24])([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17](=[S:32])[NH2:18])=[CH:15][CH:16]=1)[NH:6][C:7](=[O:9])[CH3:8])[CH3:23]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 640014propanedioic acid, (acetylamino)[(4-cyanophenyl)methyl]-, diethyl ester

Product 1

HCID 13021420HCID 13021420, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into a solution of 10.0 g (30 mmoles) of N-acetyl-4-cyano-α-(ethoxycarbonyl)phenylalanine ethyl ester and 3.5 g (35 mmoles) of triethylamine in 250 ml of pyridine, hydrogen sulfide gas is introduced until the solution is saturated. The reaction mixture is then stirred at 25° for 18 hours, followed by evaporation of the solvent. The residue is slurried with 50 ml of carbon disulfide for 1 hour and the resulting crystalline solid recovered by filtration to yield 8.7 g (24 mmoles 80%) of N-acetyl-α-ethoxycarbonyl-4-thiocarbamoylphenylalanine ethyl ester, m.p. 168°-172°.

Workup

  1. customfollowed by evaporation of the solvent
  2. waitThe residue is slurried with 50 ml of carbon disulfide for 1 hour
  3. filtrationthe resulting crystalline solid recovered by filtration

Sources & evidence

ORD record
ord-04d7160f747d4718b2564322447d356c
Source dataset
uspto-grants-1979_05
Patent number
US04156734

Reaction notes

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