Trifluoroacetic acid → 2-amino-N,N-dimethyl-1,3-thiazole-4-carboxamide

HRID 32848Notes

Reaction equation

HRID 32848 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[O:17])[N:14]([CH3:16])[CH3:15])[N:12]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:15][N:14]([CH3:16])[C:13]([C:11]1[N:12]=[C:8]([NH2:7])[S:9][CH:10]=1)=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86603401(4-Dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester

Product 1

HCID 545942972-amino-N,N-dimethyl-1,3-thiazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester (0.26 g, 0.95 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (10 mL, 130 mmol). The reaction mixture was stirred at room temperature for 2 hours, then concentrated under reduced pressure. Saturated aqueous sodium bicarbonate solution (50 mL) was added to neutralize the residue. The mixture was extracted with ethyl acetate (2×100 mL). The organic layers were separated, combined and dried over sodium sulfate, concentrated under reduced pressure and dried in vacuo to give crude 2-amino-thiazole-4-carboxylic acid dimethylamide as a yellow gum which was used without further purification (0.14 g, 86%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionSaturated aqueous sodium bicarbonate solution (50 mL) was added
  3. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  4. customThe organic layers were separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customdried in vacuo

Sources & evidence

ORD record
ord-59b9142b2dfd4e709574f6b0fc9ce70e
Source dataset
uspto-grants-2008_09
Patent number
US07427635B2

Reaction notes

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