Boron tribromide → HCID 14390905, compound

HRID 2292370Notes

Reaction equation

HRID 2292370 reaction equation
[NH2:1][C:2]([N:4]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([O:17]C)[CH:10]=2)[C:5]1=[O:19])=[O:3].B(Br)(Br)Br>ClCCl>[NH2:1][C:2]([N:4]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([OH:17])[CH:10]=2)[C:5]1=[O:19])=[O:3]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21277164HCID 21277164, compound

Product 1

HCID 14390905HCID 14390905, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 14 g (52.8 mmol) of 1-(aminocarbonyl)-3-(3,4-dimethoxyphenyl)-2-imidazolidinone in 700 ml of dichloromethane was cooled to -78° C., and 39.7 g (158 mmol) of boron tribromide was added dropwise. The dry-ice bath was removed and the reaction mixture was stirred overnight at ambient temperature. The mixture was cooled to 0° C., and 20 ml of water was added dropwise. The precipitate was filtered off by suction and stirred with water for one hour. The product was filtered off and dried in vacuo; yield: 8.51 g; melting point >250° C.

Workup

  1. customThe dry-ice bath was removed
  2. temperatureThe mixture was cooled to 0° C.
  3. addition20 ml of water was added dropwise
  4. filtrationThe precipitate was filtered off by suction
  5. stirringstirred with water for one hour
  6. filtrationThe product was filtered off
  7. customdried in vacuo

Sources & evidence

ORD record
ord-21f2dfdfbc8f4383929b619dff137d67
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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