Boron tribromide → HCID 14860701, compound

HRID 1768690Notes

Reaction equation

HRID 1768690 reaction equation
[C:1]([NH:4][CH:5](OCC)[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])(=[O:3])[CH3:2].B(Br)(Br)[Br:20]>C(Cl)Cl>[C:1]([NH:4][CH:5]([Br:20])[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 14212862HCID 14212862, compound

Product 1

HCID 14860701HCID 14860701, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-acetamido-2-ethoxy-N-benzylacetamide (2.00 g, 8 mmol) in dry CH2Cl2 (200 mL) was stirred at room temperature as a solution of BBr3 (8.8 mL, 8.8 mmol, 1.0M in CH2Cl2) was introduced by means of a syringe under a nitrogen atmosphere. A white mist formed and after it disappeared, the N2 line was removed and the reaction sealed. The resulting yellow solution was stirred (3.5 h) and then concentrated in vacuo to give yellow crystals of α-acetamido-2-bromo-N-benzyl acetamido which was stored under vacuum overnight.

Workup

  1. additionwas introduced by means of a syringe under a nitrogen atmosphere
  2. customA white mist formed
  3. customthe N2 line was removed
  4. customthe reaction sealed
  5. concentrationconcentrated in vacuo
  6. customto give yellow crystals of α-acetamido-2-bromo-N-benzyl acetamido which
  7. customwas stored under vacuum overnight

Sources & evidence

ORD record
ord-8392f2bf7bd948d4a3b64d640528453b
Source dataset
uspto-grants-1995_01
Patent number
US05378729

Reaction notes

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