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

HRID 1051420Notes

Reaction equation

HRID 1051420 reaction equation
C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])=CC=1.[S:18]1[CH:22]=[C:21](C(O)=O)[N:20]=[CH:19]1.C([N:28]([CH2:31]C)CC)C.[C:33]([OH:37])([CH3:36])([CH3:35])[CH3:34]>>[S:18]1[CH:22]=[C:21]([NH:28][C:31](=[O:8])[O:37][C:33]([CH3:36])([CH3:35])[CH3:34])[N:20]=[CH:19]1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 3042714-Thiazolecarboxylic acid

Product 1

HCID 53241636tert-butyl N-(1,3-thiazol-4-yl)carbamateYield 60.6%

Conditions

Temperature
90 °C

Procedure

DPPA (1.19 g, 4.34 mmol) was added dropwise to a mixture of thiazole-4-carboxylic acid (0.5 g, 3.87 mmol) and triethylamine (0.44 g, 4.30 mmol) in tert-BuOH (50 mL) at 0° C.-5° C. The mixture was heated to 90° C. for overnight. The solvent was evaporated in vacuo, the residue was diluted with water and extracted with EA (3×20 mL). The combined organic phase was washed with brine, dried with Na2SO4, concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography on silica gel (EA/heptane=1/10) to give the title compound (0.47 g, 2.35 mmol, 60.6%) as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with EA (3×20 mL)
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto give crude product
  8. customThe crude product was purified by column chromatography on silica gel (EA/heptane=1/10)

Sources & evidence

ORD record
ord-47f4a7c4c4584fe0842e94ae82ea0d91
Source dataset
uspto-grants-2016_07
Patent number
US09388180B2

Reaction notes

Loading…