HCID 86586329, compound → HCID 23560819, compound

HRID 1058367Notes

Reaction equation

HRID 1058367 reaction equation
[OH:1][CH2:2][C:3]1[S:7][C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:5][C:4]=1[C:16]([F:19])([F:18])[F:17]>C(#N)C.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[S:7][C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:5][C:4]=1[C:16]([F:18])([F:17])[F:19])=[O:1]

Participants

4

Reactant 1

HCID 86586329HCID 86586329, compound

Product 1

HCID 23560819HCID 23560819, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

Manganese dioxide (1.0 g, 11.5 mmol) was added to a stirred solution of crude (5-hydroxymethyl-4-trifluoromethylthiazol-2-yl)carbamic acid, 1,1-dimethylethyl ester (Example 29; 480 mg, 1.6 mmol) in acetonitrile (20 mL). The mixture was allowed to stir at room temperature for 1 h and then a further portion of manganese dioxide (0.50 g, 5.75 mmol) was added. The reaction mixture was stirred at room temperature for 1 h, it then it was filtered through Celite® and the filter pad was washed with acetonitrile. The filtrate was evaporated to dryness to give (5-formyl-4-trifluoromethylthiazol-2-yl)carbamic acid, 1,1-dimethylethyl ester (480 mg). Examination of the crude product by NMR indicated the presence of approximately 33% of (5-ethoxycarbonyl-4-trifluoromethylthiazol-2-yl)carbamic acid, 1,1-dimethylethyl ester. This mixture was used without further purification in a subsequent transformation.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. filtrationit then it was filtered through Celite®
  3. washthe filter pad was washed with acetonitrile
  4. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-6af344d982ce470da61088087f91a0dd
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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