Acetic Anhydride → 4-Acetamidothiazole

HRID 1051421Notes

Reaction equation

HRID 1051421 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.Cl.[S:9]1[CH:13]=[C:12]([NH2:14])[N:11]=[CH:10]1.C(N(CC)CC)C>C(Cl)Cl.O>[S:9]1[CH:13]=[C:12]([NH:14][C:5](=[O:7])[CH3:6])[N:11]=[CH:10]1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68841472Thiazol-4-amine hydrochloride

Product 1

HCID 202940374-Acetamidothiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (153 mg, 1.50 mmol) was added to the solution of thiazol-4-amine hydrochloride from example 2.2 (100 mg, 1.0 mmol) and triethylamine (152 mg, 1.50 mmol) in DCM (5 mL). The solution was stirred for overnight at room temperature. The reaction mixture was diluted with water, washed with 0.1 M HCl (10 mL), NaHCO3 solution and brine. The combined organic layers were dried with Na2SO4, filtered and concentrated. The resulting mixture was deposited onto silica gel and loaded onto a silica gel column and eluted with EA/PE (1:2) to aim product (55 mg, 0.39 mmol, 38.7%).

Workup

  1. washwashed with 0.1 M HCl (10 mL), NaHCO3 solution and brine
  2. dry with materialThe combined organic layers were dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluted with EA/PE (1:2)

Sources & evidence

ORD record
ord-378b4c25c35a4c78ab8253f496edd2e5
Source dataset
uspto-grants-2016_07
Patent number
US09388180B2

Reaction notes

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