Pyridine → 2-Formylamino-4-chloromethylthiazole

HRID 1252048Notes

Reaction equation

HRID 1252048 reaction equation
Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8][Cl:9])[N:7]=1.N1C=CC=CC=1.CN(C)[CH:18]=[O:19].C(OC(=O)C)=O>O>[CH:18]([NH:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8][Cl:9])[N:7]=1)=[O:19]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 75269Acetic-formic anhydride

Product 1

HCID 103749692-Formylamino-4-chloromethylthiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-amino-4-chloromethylthiazole hydrochloride (2 g), anhydrous pyridine (3.2 g) and anhydrous N,N-dimethylformamide (10 ml) was slowly added acetic formic anhydride (1.7 g) with stirring at 0° to 5° C. After one hour of stirring, the reaction mixture was poured into cold water and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and aqueous sodium chloride solution successively and dried over magnesium sulfate. The solvent was then distilled off and the residue was collected and dried to give 2-formylamino-4-chloromethylthiazole (0.94 g).

Workup

  1. stirringAfter one hour of stirring
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 1N hydrochloric acid and aqueous sodium chloride solution successively
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was then distilled off
  6. customthe residue was collected
  7. customdried

Sources & evidence

ORD record
ord-3433127cf1e74b63be700ee89918855c
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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