Potassium Carbonate → 2-Amino-4-(4-nitrophenylthiomethyl)thiazole

HRID 1656941Notes

Reaction equation

HRID 1656941 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[NH2:12][C:13]1[S:14][CH:15]=[C:16]([CH2:18]Cl)[N:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:12][C:13]1[S:14][CH:15]=[C:16]([CH2:18][S:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 158094-NitrobenzenethiolHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)

Product 1

HCID 189547312-Amino-4-(4-nitrophenylthiomethyl)thiazoleYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-nitrothiophenol (9.3 g), 2-amino-4-chloromethylthiazole hydrochloride (11 g) and potassium carbonate (20 g) in N,N-dimethylformamide (200 ml) was heated at 85°-90° C. for 5 hours with stirring. The reaction mixture was concentrated under reduced pressure and the residue was triturated with water. The precipitates were collected by filtration, washed with water and dried in vacuo to give 2-amino-4-[4-nitrophenylthiomethyl)thiazole (15.80 g, yield: 98.6%). IR (Nujol): 3400, 3100, 1630, 1530, 1340 cm-1

Workup

  1. temperaturewas heated at 85°-90° C. for 5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was triturated with water
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-b0735a7c4f8d449faa2c8ceb17bf2dbb
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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