Water → 5-Chlorothiazole-2-ethanone

HRID 1178207Notes

Reaction equation

HRID 1178207 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](OC)([O:9]C)[CH3:8])=[N:4][CH:3]=1.FC(F)(F)C(O)=O.O>ClCCl>[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 58974704HCID 58974704, compound

Product 1

HCID 299397295-Chlorothiazole-2-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-Chloro-2-(1,1-dimethoxy-ethyl)-thiazole (3.5 g) in dichloromethane (20 ml) was added trifluoroacetic acid (30 ml) and water (1 ml). The resulting mixture was stirred overnight at ambient, concentrated to an oil, diluted with diethyl ether, washed with 10% sodium bicarbonate, water and brine, dried (magnesium sulfate), filtered and concentrated to afford the sub-titled compound as a yellow solid in quantitative yield (2.6 g); 1H NMR (400 Mhz, CDCl3) δ 2.7 (3H, s), 7.8 (1H, s).

Workup

  1. concentrationconcentrated to an oil
  2. additiondiluted with diethyl ether
  3. washwashed with 10% sodium bicarbonate, water and brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-31c589ad82a64b609705114404987e8b
Source dataset
uspto-grants-2007_10
Patent number
US07276502B2

Reaction notes

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