Water → tert-Butyl thiophen-3-ylcarbamate

HRID 2080024Notes

Reaction equation

HRID 2080024 reaction equation
[S:1]1[CH:5]=[CH:4][C:3](C(O)=O)=[CH:2]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:28]([CH2:31]C)CC)C.[OH2:33].[C:34]([OH:38])([CH3:37])([CH3:36])[CH3:35]>>[C:34]([O:38][C:31](=[O:33])[NH:28][C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)([CH3:37])([CH3:36])[CH3:35]

Participants

6

Reactant 5

HCID 962WaterHCID 6386tert-ButanolHCID 6918Thiophene-3-carboxylic acidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 736476tert-Butyl thiophen-3-ylcarbamateYield 86%

Procedure

Thiophene-3-carboxylic acid (2.50 g, 19.5 mmol), diphenylphosphoryl azide (4.62 mL, 21.5 mmol), triethylamine (3.26 mL, 23.4 mmol) were dissolved in tert-butanol (50 mL), and the solution was stirred for 3.5 hours under reflux. Water was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=10:1), and the title compound (3.33 g, 16.7 mmol, 86%) was obtained as a white solid.

Workup

  1. temperatureunder reflux
  2. extractionwhich was then extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-80ebde0cd70448b7b48010cd2c2a334c
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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