N-Butylaniline → Butylphenylcarbamoyl chloride

HRID 970631Notes

Reaction equation

HRID 970631 reaction equation
[CH2:1]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[Cl:12][C:13](Cl)([O:15]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH2:1]([N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:13]([Cl:12])=[O:15])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14310N-ButylanilineHCID 94429Triphosgene

Product 1

HCID 11435782Butylphenylcarbamoyl chlorideYield 191.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6.72 g (45 mmol) of butylphenylamine in 50 ml of methylene chloride cooled to 10° C. was added slowly with stirring 6.67 g (22.5 mmol) of triphosgene in 40 ml of methylene chloride. The reaction was allowed to continue at room temperature for 27 hours. The solvent was evaporated and the residue extracted twice with n-hexane. The organic solution was concentrated in vacuo to yield 9.11 g (43.03 mmol) of a yellow oil (96%). 1H-NMR (CDCl3):δ 0,9 (m, 3H), 1,3 (m, 2H), 1,6 (m, 2H), 3,7 (m, 2H), 7,2–7,4 (m, 5H).

Workup

  1. additionwas added slowly
  2. customThe solvent was evaporated
  3. extractionthe residue extracted twice with n-hexane
  4. concentrationThe organic solution was concentrated in vacuo

Sources & evidence

ORD record
ord-6c5b672b2ee24746bc18c90b7be2f1e7
Source dataset
uspto-grants-2007_12
Patent number
US07312231B2

Reaction notes

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