HCID 10909824, compound → 4-Isopropylthiazole-5-carbaldehyde

HRID 1058366Notes

Reaction equation

HRID 1058366 reaction equation
[CH3:1][CH:2]([C:4]1[N:5]=[CH:6][S:7][C:8]=1[CH2:9][OH:10])[CH3:3]>C(#N)C.[O-2].[O-2].[Mn+4]>[CH3:1][CH:2]([C:4]1[N:5]=[CH:6][S:7][C:8]=1[CH:9]=[O:10])[CH3:3]

Participants

4

Reactant 1

HCID 10909824HCID 10909824, compound

Product 1

HCID 110841114-Isopropylthiazole-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

Portions of manganese dioxide (330 mg, 3.8 mmol) were added to a stirred solution of 4-(1-methylethyl)thiazole-5-methanol (Example 26; 330 mg, 2.1 mmol) in acetonitrile (10 mL) at hourly intervals for 4 h. One h after the last addition, the reaction mixture was filtered through Celite® and evaporated to dryness to give 4-(1-methylethyl)thiazole-5-carboxaldehyde (360 mg, 110% of the theoretical amount). Examination of the product by NMR indicated the presence of acetonitrile. This material was used with further purification in subsequent transformations.

Workup

  1. additionOne h after the last addition
  2. filtrationthe reaction mixture was filtered through Celite®
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-d3709346b06c45b5bbb5a5ff42bd23ad
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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