tert-Butanol → tert-butyl N-(1,3-thiazol-4-yl)carbamate

HRID 2369369Notes

Reaction equation

HRID 2369369 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.P(N=[N+]=[N-])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=[O:9].[S:27]1C=C(C(O)=O)[N:29]=[CH:28]1.[C:35]([OH:39])([CH3:38])([CH3:37])[CH3:36]>>[S:27]1[CH:7]=[C:6]([NH:3][C:4](=[O:9])[O:39][C:35]([CH3:38])([CH3:37])[CH3:36])[N:29]=[CH:28]1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 3042714-Thiazolecarboxylic acid

Product 1

HCID 53241636tert-butyl N-(1,3-thiazol-4-yl)carbamateYield 94%

Procedure

5.80 ml (41.84 mmol) of triethylamine and subsequently, with ice-bath cooling, 9.10 ml (42.19 mmol) of diphenyl azidophosphate are introduced into a solution of 4.85 g (37.55 mmol) of 4-thiazolecarboxylic acid in 180 ml of tert-butanol under nitrogen, and the reaction mixture is heated under reflux for 16 h. The solvent is removed in vacuo, the residue is taken up in dichloromethane and washed twice with water and saturated NaCl solution. The organic phase is dried over sodium sulfate, evaporated in vacuo, and the residue is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1/1), giving 7.07 g (35.30 mmol, 94%) of tert-butyl N-(1,3-thiazol-4-yl)carbamate as beige crystals; ESI-MS: m/e: 201 ([M+H]+).

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 16 h
  3. customThe solvent is removed in vacuo
  4. washwashed twice with water and saturated NaCl solution
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customevaporated in vacuo
  7. customthe residue is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1/1)

Sources & evidence

ORD record
ord-6f9f90ec173f4a8cb5e9370bcec38852
Source dataset
uspto-grants-2014_04
Patent number
US08703961B2

Reaction notes

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