2-[(2,3-Dimethylphenoxy)methyl]-4,5-dihydro-1H-imidazole → HCID 23337898, compound

HRID 903161Notes

Reaction equation

HRID 903161 reaction equation
[CH3:1][C:2]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]1[NH:7][CH2:8][CH2:9][N:10]=1.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1>C(Cl)Cl>[OH2:4].[Br: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][O: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

4

Reactant 2

HCID 498352-[(2,3-Dimethylphenoxy)methyl]-4,5-dihydro-1H-imidazoleHCID 756094-Bromophenyl isocyanate

Product 1

HCID 23337898HCID 23337898, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(2,3-dimethylphenoxymethyl)-2-imidazoline (20.4 g; 1.0 mol) in methylene chloride (300 ml) was cooled to -65° C. and a solution of 4-bromophenylisocyanate (19.8 g; 1.0 mol) in methylene chloride (300 ml) added dropwise during 30 minutes. The reaction mixture was then allowed to warm to ambient temperature and left to stand for 2 hours, when a precipitate had formed. The reaction mixture was evaporated under reduced pressure and the residue recrystallised from acetone to give 1-(N-(4-bromophenyl)-carbamoyl)-2-(2,3-dimethylphenoxymethyl)-2-imidazoline monohydrate, m.p. 150°-151° C.

Workup

  1. waitleft
  2. customwhen a precipitate had formed
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customthe residue recrystallised from acetone

Sources & evidence

ORD record
ord-e7b3663166df469894b712abb71571de
Source dataset
uspto-grants-1980_10
Patent number
US04226876

Reaction notes

Loading…