Hydrochloric Acid → N'-(3-Benzoylphenyl)-N,N-dimethylurea

HRID 2398917Notes

Reaction equation

HRID 2398917 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[NH2:7][C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][CH:21]=1)[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].Cl>CN(C)C=O.C(N(CC)CC)C>[C:11]([C:10]1[CH:9]=[C:8]([NH:7][C:3](=[O:4])[N:2]([CH3:6])[CH3:1])[CH:21]=[CH:20][CH:19]=1)(=[O:12])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6598Dimethylcarbamoyl ChlorideHCID 17817Methanone, (3-aminophenyl)phenyl-

Product 1

HCID 21431955N'-(3-Benzoylphenyl)-N,N-dimethylurea

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

Dimethylcarbamoyl chloride (7.5 grams, 0.07 mole) was added to a solution of 3-aminobenzophenone (10 grams, 0.05 mole) in dimethylformamide (150 ml.), triethylamine (10 ml.) at 10° C. with stirring and ice cooling. The reaction temperature was next raised to 60° C. for 20 hours, then cooled and poured onto ice water (500 grams) containing dilute hydrochloric acid. A tarry solid was obtained by decanting off the aqueous organic solution. Purification was effected by dissolving the tarry solid in methylene chloride and passing through a silica gel dry column - eluent methylene chloride. On elution with dichloromethane, the product, 3(-m-benzoylphenyl)-1,1-dimethyl urea, is obtained. Melting point was 104° C.-105° C. Crystallization from benzene-hexane (9:1) mixture gave solid 109° C.-110° C., which on benzene-hexane crystallizations afforded a melting point of from 121° C. to 122° C. identified as the desired urea by comparison with the sample prepared from phosgene and dimethylamine.

Workup

  1. temperaturecooled
  2. additionpoured onto ice water (500 grams)
  3. customA tarry solid was obtained
  4. customby decanting off the aqueous organic solution
  5. customPurification
  6. dissolutionby dissolving the tarry solid in methylene chloride
  7. washOn elution with dichloromethane

Sources & evidence

ORD record
ord-c882b85ccaf749dca27ea48bbc4b753a
Source dataset
uspto-grants-1977_05
Patent number
US04026697

Reaction notes

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