1-Butanol → Diphenylacetyl-carbamic acid butyl ester

HRID 392686

Reaction equation

HRID 392686 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[C:6]1([CH:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]([N:15]=[C:16]=[O:17])=[O:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl>[CH2:1]([O:5][C:16](=[O:17])[NH:15][C:13](=[O:14])[CH:12]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 2631-ButanolHCID 11264874Diphenylacetyl isocyanate

Product 1

HCID 9883204Diphenylacetyl-carbamic acid butyl esterYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-butanol (0.32 ml, 3.49 mmol) in dichloromethane (4 ml) was added a solution of diphenylacetyl isocyanate (2.33 ml, 0.5M in CH2Cl2, 1.16 mmol) and the mixture was stirred at RT for 1 h. Removal of the solvent in vacuum left a yellow oil, which was purified by column chromatography on silica gel (ethyl acetate/hexane 1:2) to give the title compound (0.3 g, 83%) as a light yellow solid, m.p. 82-84° C. and MS: m/e=334 (M+Na+).

Workup

  1. customRemoval of the solvent in vacuum
  2. waitleft a yellow oil, which
  3. customwas purified by column chromatography on silica gel (ethyl acetate/hexane 1:2)

Sources & evidence

ORD record
ord-c63e3bc3941d4ebd8d04e15890bd6770
Source dataset
uspto-grants-2004_10
Patent number
US06803381B1

Linked notes

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