Water → HCID 87166384, compound

HRID 1754977Notes

Reaction equation

HRID 1754977 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].C(N(CC)C(C)C)(C)C.[CH2:14]([O:21][CH2:22][CH2:23][NH:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([Br:32])=[C:27]([CH3:33])[CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C1(C)C=CC=CC=1>[CH2:14]([O:21][CH2:22][CH2:23][N:24]([C:25]1[CH:26]=[C:27]([CH3:33])[C:28]([Br:32])=[C:29]([CH3:31])[CH:30]=1)[C:1]([Cl:4])=[O:2])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 66817209HCID 66817209, compound

Product 1

HCID 87166384HCID 87166384, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosgene (3.5 ml, 6.64 mmol, 20% solution in toluene) and N,N-diisopropylethylamine (1.2 ml, 6.64 mmol) were added to a solution of N-(2-(benzyloxy)ethyl)-4-bromo-3,5-dimethylaniline (740 mg, 2.21 mmol) in anhydrous toluene (11 ml) at 0° C. The reaction solution was gradually warmed to room temperature and stirred at the same temperature for three hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic phase was sequentially washed with water and saturated brine and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane) to give N-(2-(benzyloxy)ethyl)-N-(4-bromo-3,5-dimethylphenyl)carbamic acid chloride (860 mg, 98%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic phase was sequentially washed with water and saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (dichloromethane)

Sources & evidence

ORD record
ord-5915a7d822e34e7a878c1f4361f6f75a
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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