2-Amino-5-chlorobenzophenone → N-(2-Benzoyl-4-chlorophenyl)-N′-(1-methylethyl)urea

HRID 128029Notes

Reaction equation

HRID 128029 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH:17]([N:20]=[C:21]=[O:22])([CH3:19])[CH3:18]>CCCCCC>[C:4]([C:3]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:2]=1[NH:1][C:21]([NH:20][CH:17]([CH3:19])[CH3:18])=[O:22])(=[O:5])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 128702-Amino-5-chlorobenzophenoneHCID 61277Isopropyl isocyanate

Product 1

HCID 12750795N-(2-Benzoyl-4-chlorophenyl)-N′-(1-methylethyl)ureaYield 63%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 14 g (0.06 mole) of 2-amino-5-chlorobenzophenone and 40 ml of isopropyl isocyanate was refluxed for 3 hrs. The solid that formed was suspended in 25 ml of hexane, and then collected on a filter and recrystallized from ethanol to give 12.0 g (63%) of 1-(2-benzoyl-4-chlorophenyl)-3-isopropylurea as colorless needles: mp 190°-192°; 1H nmr (CDDl3) δ1.19 ppm (d, J=6 Hz, 6H), 3.98 ppm (m, 1H), 4.95 ppm (m, NH), 7.2-7.8 ppm (m, 7H), 8.5 ppm (d, J=10 Hz, 1H) and 10.1 ppm (NH); 13C nmr (DMSO-d6) δ195.4 ppm (C=O) and 153.9 ppm (NHCO).

Workup

  1. temperaturewas refluxed for 3 hrs
  2. customThe solid that formed
  3. customcollected on
  4. filtrationa filter
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-00b9212ab22b4b9cbaf86bf8ad15f599
Source dataset
uspto-grants-1981_03
Patent number
US04258187

Reaction notes

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