Phenyl isocyanate → HCID 12919024, compound

HRID 903158Notes

Reaction equation

HRID 903158 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.[C:16]1([N:22]=[C:23]=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[C:16]1([NH:22][C:23]([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:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 498352-[(2,3-Dimethylphenoxy)methyl]-4,5-dihydro-1H-imidazole

Product 1

HCID 12919024HCID 12919024, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(2,3-dimethylphenoxymethyl)-2-imidazoline (20.4 g; 1.0 moles) in methylene chloride (300 ml) was cooled to -65° C. and a solution of phenylisocyanate (11.9 g; 1.0 moles) 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-phenylcarbamoyl-2-(2,3-dimethylphenoxymethyl)-2-imidazoline, m.p. 150°-152° 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-efaa14a0f5c74aaab5dea4086164ce82
Source dataset
uspto-grants-1980_10
Patent number
US04226876

Reaction notes

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