4-Chlorophenyl Isocyanate → 1-(N-(4-chlorophenyl)-carbamoyl)-2-(2,3-dimethylanilinomethyl)-2-imidazoline

HRID 903160Notes

Reaction equation

[CH3:1][C:2]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:3]=1[NH:4][CH2:5][C:6]1[NH:7][CH2:8][CH2:9][N:10]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1>C(Cl)Cl>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([N:10]2[CH2:9][CH2:8][N:7]=[C:6]2[CH2:5][NH:4][C:3]2[CH:11]=[CH:12][CH:13]=[C:14]([CH3:15])[C:2]=2[CH3:1])=[O:25])=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(2,3-Dimethylanilinomethyl)-2-imidazoline (4.20 g; 0.024 moles) was stirred in methylene chloride (90 ml), cooled to 0° C. and a solution of 4-chlorophenyl isocyanate (3.66 g; 0.024 moles) in methylene chloride (10 ml) was then added dropwise. A white precipitate formed rapidly. Stirring was continued for 2 to 3 hours after the addition at 0° C., the reaction mixture then allowed to reach ambient temperature and stirring was continued overnight. The reaction mixture was then evaporated to dryness under reduced pressure and the solid residue so obtained recrystallised from propan-2-ol to yield white crystals of 1-(N-(4-chlorophenyl)-carbamoyl)-2-(2,3-dimethylanilinomethyl)-2-imidazoline m.p. 153°-155° C.

Workup

customA white precipitate formed rapidly
additionafter the addition at 0° C.
customto reach ambient temperature
stirringstirring
waitwas continued overnight
customThe reaction mixture was then evaporated to dryness under reduced pressure
customthe solid residue so obtained
customrecrystallised from propan-2-ol

Sources & evidence

ORD record: ord-a0b106ecdabb40daa1137581a50e9d68
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04226876

Reaction notes

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