N-Butylaniline → Butylphenylcarbamoyl chloride

HRID 502802

Reaction equation

HRID 502802 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-d74b70a9d464441a9e41e7dddeb23ff4
Source dataset
uspto-grants-2010_08
Patent number
US07776879B2

Linked notes

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