Acetic Anhydride → N-(thiazol-5-yl)acetamide

HRID 1051416Notes

Reaction equation

HRID 1051416 reaction equation
CCN(CC)CC.Cl.[S:9]1[C:13]([NH2:14])=[CH:12][N:11]=[CH:10]1.[CH3:15][C:16](OC(C)=O)=[O:17]>C(Cl)Cl>[S:9]1[C:13]([NH:14][C:16](=[O:17])[CH3:15])=[CH:12][N:11]=[CH:10]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 467381465-Thiazolamine hydrochloride

Product 1

HCID 19779166N-(thiazol-5-yl)acetamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Et3N (0.31 mL, 2.20 mmol) and thiazol-5-amine hydrochloride (0.2 g, 1.46 mmol) from example 1.2 in DCM (10 mL) was added Ac2O (0.21 mL, 2.20 mmol). The mixture was stirred at room temperature for 3 h and then concentrated. The resulting mixture was deposited onto silica gel and loaded onto a silica gel column and eluted with EA to give the title compound (0.14 g, 0.98 mmol, 70%).

Workup

  1. concentrationconcentrated
  2. washeluted with EA

Sources & evidence

ORD record
ord-942b5baf06304a5ab557748029df7e00
Source dataset
uspto-grants-2016_07
Patent number
US09388180B2

Reaction notes

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