(4-Hydroxymethylthiazol-2-yl)carbamic acid tert-butyl ester → (4-Formylthiazol-2-yl)carbamic acid tert-butyl ester

HRID 1787661Notes

Reaction equation

HRID 1787661 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][OH:14])[N:12]=1)([CH3:4])([CH3:3])[CH3:2]>ClCCl>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[S:9][CH:10]=[C:11]([CH:13]=[O:14])[N:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 22280475(4-Hydroxymethylthiazol-2-yl)carbamic acid tert-butyl ester

Product 1

HCID 23138686(4-Formylthiazol-2-yl)carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Hydroxymethyl-thiazol-2-yl)-carbamic acid tert-butyl ester (1.62 g, 6.95 mmol) was dissolved in 30 ml dichloromethane. Mangan(IV)oxid (3.65 g, 41.7 mmol) was added and the reaction mixture stirred at reflux for 2 hrs. The suspension was filtered through a dicalite speed plus pad and washed with dichloromethane. The solvents were evaporated and the desired compound was obtained as a light yellow solid (1.25 g, 78%), MS: m/e=229.2 (M+H+).

Workup

  1. temperatureat reflux for 2 hrs
  2. filtrationThe suspension was filtered through a dicalite speed plus pad
  3. washwashed with dichloromethane
  4. customThe solvents were evaporated

Sources & evidence

ORD record
ord-054c0bf3890b4d6aae392ca69d1292e4
Source dataset
uspto-grants-2009_03
Patent number
US07511055B2

Reaction notes

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