Boron tribromide → HCID 14880504, compound

HRID 1588841Notes

Reaction equation

HRID 1588841 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:32])[NH:15][CH2:16][C:17]([N:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:18])[CH:10]=[CH:11][CH:12]=1>ClCCl>[OH:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:32])[NH:15][CH2:16][C:17]([N:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:18])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 14880503HCID 14880503, compound

Product 1

HCID 14880504HCID 14880504, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-50 °C

Procedure

A 1M methylene chloride solution (25 cc) of boron tribromide is added in the course of 15 minutes at a temperature in the region of -50° C. to a solution, maintained under a nitrogen atmosphere, of 2-[3-(3-methoxyphenyl)ureido]-N,N-diphenylacetamide (1.6 g) in dichloromethane (25 cc). The mixture obtained is stirred for 2 hours at a temperature in the region of -50° C. and then for 20 hours at a temperature in the region of 20° C. The precipitate formed is separated by filtration, washed with distilled water (6×10 cc) and dried in the air. After recrystallization in acetonitrile, 2-[3-(3-hydroxyphenyl)ureido]-N,N-diphenylacetamide (0.5 g), m.p. 244° C., is obtained.

Workup

  1. customThe mixture obtained
  2. waitfor 20 hours at a temperature in the region of 20° C
  3. customThe precipitate formed
  4. customis separated by filtration
  5. washwashed with distilled water (6×10 cc)
  6. customdried in the air
  7. customAfter recrystallization in acetonitrile

Sources & evidence

ORD record
ord-971865fc83e94764a30a1ee554395ca5
Source dataset
uspto-grants-1993_06
Patent number
US05223529

Reaction notes

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