Boron tribromide → N-Benzyl-N-butyl-N'-(3-chloro-2-hydroxyphenyl)urea

HRID 359978Notes

Reaction equation

HRID 359978 reaction equation
[CH2:1]([N:8]([CH2:21][CH2:22][CH2:23][CH3:24])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=1[O:19]C)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl.O>[CH2:1]([N:8]([CH2:21][CH2:22][CH2:23][CH3:24])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=1[OH:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 13732989N-Benzyl-N-butyl-N'-(3-chloro-2-methoxyphenyl)urea

Product 1

HCID 13732993N-Benzyl-N-butyl-N'-(3-chloro-2-hydroxyphenyl)urea

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.73 g of 1-benzyl-1-(n-butyl)-3-(2-methoxy-3-chlorophenyl)urea and 1.0 ml of boron tribromide in 40 ml of methylene chloride was stirred at ambient temperature for 3 days and diluted with water. The organic layer was separated, dried, and evaporated. The residue was crystallized from hexane to yield 1-benzyl1-(n-butyl)-3-(2-hydroxy-3-chlorophenyl)urea, m.p. 59°-62° C.

Workup

  1. customThe organic layer was separated
  2. customdried
  3. customevaporated
  4. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-eec7567e72214a308ec19094a57fb68c
Source dataset
uspto-grants-1991_03
Patent number
US05003106

Reaction notes

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