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Phenyl-1-naphthylamine → N'-Methyl-N-naphthalen-1-yl-N-phenylurea

HRID 620470
Notes
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Reaction equation

HRID 620470 reaction equation
[C:1]1([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:18][N:19]=[C:20]=[O:21]>C1(C)C=CC=CC=1.P([O-])(OCCCC)(OCCCC)=O>[CH3:18][NH:19][C:20]([N:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)=[O:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7013Phenyl-1-naphthylamineHCID 12228Methyl Isocyanate

Product 1

HCID 14204126N'-Methyl-N-naphthalen-1-yl-N-phenylureaYield 80%

Reagents, catalysts & solvents 2

HCID 3790919Dibutyl phosphate anionCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

0.5 mole of α-naphthyl-phenylamine 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 warmed at 100° C. for 24 hours, with stirring, and then cooled to 10° C. After the product had been filtered off, washed with 150 ml of cold toluene and dried, 0.4 mole of N-methyl-N'-phenyl-N'-α-naphthyl-urea was obtained. Melting point: 146° C./yield: 80% of theory,

Workup

  1. temperaturecooled to 10° C
  2. filtrationAfter the product had been filtered off
  3. washwashed with 150 ml of cold toluene
  4. customdried

Sources & evidence

ORD record
ord-625c0446b99e477bb001c8bb684aae95
Source dataset
uspto-grants-1989_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04820871

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes