Diphenylamine → N-Methyl-N',N'-diphenylurea

HRID 620474

Reaction equation

HRID 620474 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][N:15]=[C:16]=[O:17]>C1(C)C=CC=CC=1>[CH3:14][NH:15][C:16]([N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:17]

Participants

4

Reactant 2

HCID 11487Diphenylamine2×HCID 12228Methyl Isocyanate2×

Product 1

HCID 25711N-Methyl-N',N'-diphenylureaYield 480%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

0.5 mole of diphenylamine was taken together with 0.53 mole of methyl isocyanate and 0,6 g of di-n-butyl phosphate in 150 ml of toluene. The mixture was heated at 100° C. for 10 hours, with stirring. After cooling to room temperature, the N-methyl-N',N'-diphenylurea formed was filtered off wtih suction. The filtrate was made up to 150 ml with toluene, and 0.5 mole of diphenylamine and 0.53 mole of methyl isocyanate were added. The mixture was heated again at 100° C. for 10 hours, with stirring, and then cooled to room temperature. Recycling of the filtrate and subsequent addition of in each case 0.5 mole of diphenylamine and 0.53 mole of methyl isocyanate was repeated a further three times. After these five reactions with only a single addition of catalyst, 2.4 moles of N-methyl-N',N'-diphenylurea were obtained. The urea was washed with in each case 100 ml of cold toluene after each reaction. Melting point: 170°/yield: 96% of theory.

Workup

  1. filtrationwas filtered off wtih suction
  2. additionwere added
  3. temperaturecooled to room temperature
  4. additionAfter these five reactions with only a single addition of catalyst

Sources & evidence

ORD record
ord-9717b17ba91a44a19c097861907a5eb0
Source dataset
uspto-grants-1989_04
Patent number
US04820871

Linked notes

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