Boron tribromide → HCID 14860701, compound

HRID 2256008Notes

Reaction equation

HRID 2256008 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 while mist formed and alter 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 while 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-15075a4098fb4eaea33c1118e35f7b96
Source dataset
uspto-grants-1997_08
Patent number
US05654301

Reaction notes

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