Water → HCID 20140943, compound

HRID 1252051Notes

Reaction equation

HRID 1252051 reaction equation
Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8][Cl:9])[N:7]=1.[CH3:10][N:11]=[C:12]=[O:13].N1C=CC=CC=1.O>CN(C)C=O>[CH3:10][NH:11][C:12](=[O:13])[NH:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8][Cl:9])[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 12228Methyl Isocyanate3×HCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)

Product 1

HCID 20140943HCID 20140943, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-amino-4-chloromethylthiazole hydrochloride (0.5 g) in N,N-dimethylformamide (5 ml) was added methyl isocyanate (0.17 g) in the presence of pyridine (0.24 ml). After 4 hours, methyl isocyanate (0.1 g) was further added. After 1 hour, methyl isocyanate (0.1 g) was added again and the reaction mixture was heated at 50° C. for 3.5 hours. The reaction mixture was then poured into water (20 ml) and extracted with ethyl acetate (30 ml×2). The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off and the residue was crystallized from a mixture of ethanol and n-hexane to give 2-(3-methylureido)-4-chloromethylthiazole (230 mg).

Workup

  1. waitAfter 1 hour
  2. extractionextracted with ethyl acetate (30 ml×2)
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was crystallized from a mixture of ethanol and n-hexane

Sources & evidence

ORD record
ord-ada4beb0bf4f43e8a8ee266666c7895f
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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