Dichloromethane → 1-(2-Benzoyl-4-chlorophenyl)-1-methyl-3-phenylurea

HRID 128033Notes

Reaction equation

HRID 128033 reaction equation
ClC1[CH:3]=[CH:4][C:5]([NH:16][CH3:17])=[C:6]([CH:15]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].[C:18]1([N:24]=[C:25]=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:27]([Cl:29])Cl>>[C:7]([C:6]1[CH:15]=[C:27]([Cl:29])[CH:3]=[CH:4][C:5]=1[N:16]([CH3:17])[C:25]([NH:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:26])(=[O:8])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 7672Phenyl isocyanateHCID 139252-(Methylamino)-5-chlorobenzophenone

Product 1

HCID 234716281-(2-Benzoyl-4-chlorophenyl)-1-methyl-3-phenylureaYield 66%

Procedure

A solution of 12.3 g (0.05 mole) of 5-chloro-2-methylaminobenzophenone and 11.9 g (0.1 mole) of phenyl isocyanate in 50 ml of methylene chloride was refluxed for 3 days, and then evaporated to dryness under reduced pressure. The residual syrup was stirred with ether until it crystallized. The crystals were collected on a filter and washed with ether to give 12.06 g (66%) of 1-(2-benzoyl-4-chlorophenyl)-1-methyl-3-phenylurea as light yellow crystals. A sample was recrystallized from ethanol to give colorless crystals: mp 158°-160°; 1H nmr (DMSO-d6) δ3.41 ppm (s, 3H), 6.7-7.5 ppm (m, 13H).

Workup

  1. customevaporated to dryness under reduced pressure
  2. customcrystallized
  3. customThe crystals were collected on
  4. filtrationa filter
  5. washwashed with ether

Sources & evidence

ORD record
ord-c800b6ad2fc14cb9906fc0dc171e83fc
Source dataset
uspto-grants-1981_03
Patent number
US04258187

Reaction notes

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