Boron tribromide → HCID 15229159, compound

HRID 1198386Notes

Reaction equation

HRID 1198386 reaction equation
B(Br)(Br)Br.[CH2:5]([S:7]([CH2:10][CH2:11][C:12]([NH:14][NH:15][C:16]([N:18]1[CH2:24][C:23]2[CH:25]=[CH:26][C:27]([O:29]C)=[CH:28][C:22]=2[O:21][C:20]2[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:19]1=2)=[O:17])=[O:13])(=[O:9])=[O:8])[CH3:6]>C(Cl)Cl>[CH2:5]([S:7]([CH2:10][CH2:11][C:12]([NH:14][NH:15][C:16]([N:18]1[CH2:24][C:23]2[CH:25]=[CH:26][C:27]([OH:29])=[CH:28][C:22]=2[O:21][C:20]2[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:19]1=2)=[O:17])=[O:13])(=[O:8])=[O:9])[CH3:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 15229158HCID 15229158, compound

Product 1

HCID 15229159HCID 15229159, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of boron tribromide (I.0M in 7.3 mL of methylene chloride) at approximately 5° C. (ice water bath) under nitrogen was added dropwise 1.09 g of 8-chloro-3-methoxydibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[3-(ethylsulfonyl)-1-oxopropyl]hydrazide, prepared as described above in Example 7, in 5 mL of methylene chloride. The ice bath was removed and the reaction stirred at room temperature for 3 hours. The reaction was carefully quenched by the addition of 10 mL of 1N HCl, and poured into 150 mL of ethyl acetate. The solution was washed with 150 mL of 1N HCl and brine, dried over magnesium sulfate, and evaporated in vacuo to a greenish residue. This was treated with 10 mL of ethanol (3A), and the resulting solid was collected by filtration. Recrystallization from ethanol (3A) yielded 0.58 g (54.9%) pure product as a white solid.

Workup

  1. customprepared
  2. customThe ice bath was removed
  3. customThe reaction was carefully quenched by the addition of 10 mL of 1N HCl
  4. additionpoured into 150 mL of ethyl acetate
  5. washThe solution was washed with 150 mL of 1N HCl and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo to a greenish residue
  8. additionThis was treated with 10 mL of ethanol (3A)
  9. filtrationthe resulting solid was collected by filtration
  10. customRecrystallization from ethanol (3A)

Sources & evidence

ORD record
ord-69c06c7d0518422998a22f8c476c2dbb
Source dataset
uspto-grants-1994_01
Patent number
US05281590

Reaction notes

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