Butyl isocyanate → Urea, N,N-diphenyl-N'-butyl-

HRID 620472

Reaction equation

HRID 620472 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.[CH2:14]([N:18]=[C:19]=[O:20])[CH2:15][CH2:16][CH3:17]>C1(C)C(C)=CC=CC=1.P([O-])(OCCCC)(OCCCC)=O>[CH2:14]([NH:18][C:19]([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:20])[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 8110Butyl isocyanateHCID 11487Diphenylamine

Product 1

HCID 14204127Urea, N,N-diphenyl-N'-butyl-Yield 60%

Reagents, catalysts & solvents 2

HCID 3790919Dibutyl phosphate anionCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

0.5 mole of diphenylamine was taken together with 0.53 mole of n-butyl isocyanate and 1 g of di-n-butyl phosphate in 150 ml of xylene. The mixture was heated at 120° C. for 24 hours, with stirring, and then cooled to room temperature. After the product had been filtered off, washed with 100 ml of cold xylene and dried, 0.3 mole of N-n-butyl-N',N'-diphenylurea was obtained. Melting point: 92° C./yield: 60% of theory.

Workup

  1. temperaturecooled to room temperature
  2. filtrationAfter the product had been filtered off
  3. washwashed with 100 ml of cold xylene
  4. customdried

Sources & evidence

ORD record
ord-0866a8e646a24c0499f049e1d4316866
Source dataset
uspto-grants-1989_04
Patent number
US04820871

Linked notes

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