Formic Acid → 2-(N-methylformamido)-4-methyl-5-acetylthiazole

HRID 1906018Notes

Reaction equation

HRID 1906018 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([C:9](=[O:11])[CH3:10])=[C:6]([CH3:8])[N:7]=1.[C:12](OC(=O)C)(=[O:14])C.C(O)=O>O1CCCC1>[CH3:1][N:2]([C:3]1[S:4][C:5]([C:9](=[O:11])[CH3:10])=[C:6]([CH3:8])[N:7]=1)[CH:12]=[O:14]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 227441161-(4-Methyl-2-(methylamino)thiazol-5-YL)ethanone

Product 1

HCID 201450012-(N-methylformamido)-4-methyl-5-acetylthiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methylamino-4-methyl-5-acetylthiazole (35 g) in tetrahydrofuran (700 ml) were added a mixture of acetic anhydride (94.5 ml) and formic acid (37.7 ml) at ambient temperature and the mixture was stirred for two hours. The reaction mixture was evaporated in vacuo. The residue was added to water and the resultant precipitate was collected by filtration and dried over phosphorus pentoxide to give 2-(N-methylformamido)-4-methyl-5-acetylthiazole (39.59 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. additionThe residue was added to water
  3. filtrationthe resultant precipitate was collected by filtration
  4. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-884dbaa5b4494834b8bee2ff882716a7
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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