4-Pyridinecarbothioamide → HCID 178459645, compound

HRID 1374403Notes

Reaction equation

HRID 1374403 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])[C@@H:7]([CH3:16])[CH:6]=1)=O.C(N)(=S)C1C=CN=CC=1.[C:26](=[S:29])([S-:28])[NH2:27].[NH4+]>CO>[CH3:16][C@H:7]1[CH:6]=[C:5]([C:3]2[N:27]=[C:26]([SH:29])[S:28][CH:2]=2)[CH2:9][N:8]1[C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11]

Participants

5

Reactant 3

HCID 27237884-PyridinecarbothioamideHCID 11021108HCID 11021108, compoundHCID 11083854Ammonium dithiocarbamate

Product 1

HCID 178459645HCID 178459645, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of allyl (2S)-4-(chloroacetyl)-2-methyl-2,5-dihydro-1H-pyrrole-1-carboxylate(0.15 g, 0.62 mmol) in methanol (2 ml) were added at 0–5° C. thioisonicotinamide (5 mg) and ammonium dithiocarbamate (82 mg, 0.74 mmol). The temperature was raised to room temperature and the mixture was stirred for 15 minute, followed with stirring at 55–60° C. for 1 hour. The solvent was removed under reduced pressure and the residue was washed with ethanol to give allyl (2S)-2-methyl-4-(2-mercapto-1,3-thiazol-4-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate(60 mg, 34%).

Workup

  1. stirringwith stirring at 55–60° C. for 1 hour
  2. customThe solvent was removed under reduced pressure
  3. washthe residue was washed with ethanol

Sources & evidence

ORD record
ord-69074a7e63ab48ae9e8c610516c8bd4c
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

Loading…