Toluene → HCID 12919024, compound

HRID 903159Notes

Reaction equation

HRID 903159 reaction equation
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.[CH3:12][C:13]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:14]=1[O:15][CH2:16][C:17]1[NH:18][CH2:19][CH2:20][N:21]=1.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)(Cl)Cl.C(OCC)C>[C:28]1([NH:27][C:1]([N:21]2[CH2:20][CH2:19][N:18]=[C:17]2[CH2:16][O:15][C:14]2[CH:22]=[CH:23][CH:24]=[C:25]([CH3:26])[C:13]=2[CH3:12])=[O:2])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6115AnilineHCID 6371PhosgeneHCID 498352-[(2,3-Dimethylphenoxy)methyl]-4,5-dihydro-1H-imidazole

Product 1

HCID 12919024HCID 12919024, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent2×

Procedure

A 17% solution of phosgene in toluene (3.2 g containing 0.5521 g., 0.00549 moles COCl2) in dry chloroform (15 ml) was added slowly with stirring at 0° C. to a solution of 2-(2,3-dimethylphenoxymethyl)-2-imidazoline (2.40 g, 0.0115 moles) in dry chloroform (20 ml). When addition was complete the reaction mixture was left at ambient temperature for 2 hours, diluted with an equal volume of dry diethylether and rapidly filtered. The filtrate, which contained the N-chlorocarbamoyl adduct of 2-(2,3-dimethylphenoxymethyl)-2-imidazoline, was treated with freshly distilled dry aniline (0.664 g, 0.00714 moles) and the mixture left at ambient temperature overnight at which time tlc showed that the major compound was the desired product. The mixture was evaporated to dryness in vacuo and the residue taken up in a mixture of aqueous sodium carbonate and dichloromethane. The organic layer was washed with water, dried over magnesium sulphate and evaporated to dryness to give a residue which was purified as described in (A) above to give 1-N-phenylcarbamoyl-2-(2,3-dimethylphenoxymethyl)-2-imidazoline, identical with that obtained in (A) above.

Workup

  1. additionWhen addition
  2. filtrationrapidly filtered
  3. additionwas treated
  4. waitthe mixture left at ambient temperature overnight at which time tlc

Sources & evidence

ORD record
ord-409b83a1a79f4c428593a1a1e6b5aeb7
Source dataset
uspto-grants-1980_10
Patent number
US04226876

Reaction notes

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