Ethanol → HCID 9803983, compound

HRID 1198383Notes

Reaction equation

HRID 1198383 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7][C:8]([NH:10][NH:11][C:12]([N:14]1[CH2:20][C:19]2[CH:21]=[C:22]([O:25]C)[CH:23]=[CH:24][C:18]=2[O:17][C:16]2[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:15]1=2)=[O:13])=[O:9])(=[O:5])=[O:4])[CH3:2].B(Br)(Br)Br.C(O)C>C(Cl)Cl>[CH2:1]([S:3]([CH2:6][CH2:7][C:8]([NH:10][NH:11][C:12]([N:14]1[CH2:20][C:19]2[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:18]=2[O:17][C:16]2[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:15]1=2)=[O:13])=[O:9])(=[O:4])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 25134Boron tribromideHCID 15229157HCID 15229157, compound

Product 1

HCID 9803983HCID 9803983, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 8-chloro-2-methoxydibenz-[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[3-(ethyl-sulfonyl)-1-oxopropyl]hydrazide (1.00 g), prepared in the manner described above in Example 3, in methylene chloride (5 mL) at approximately 5° C. (ice water bath) under nitrogen was added dropwise boron tribromide (1.0M in 6.7 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 1N HCl, and poured into ethyl acetate (100 mL). The solution Was washed once with 1N HCl (100 mL). The 100 mL of 1N HCl wash was extracted With ethyl acetate (100 mL). The ethyl acetate solutions were combined and washed With 1N HCl, water and brine. Evaporation of the solution in vacuo resulted in a semi-solid residue. This was treated with 10 mL of ethanol (3A) and heated on a steam bath for several minutes to break up the solid. Upon cooling, the solidified product was collected by filtration. Recrystallization from ethanol (3A) yielded 0.44 g (45%) pure product as a white solid. Melting Point: 200°14 202° C.

Workup

  1. customprepared in the manner
  2. customThe ice bath was removed
  3. customThe reaction was carefully quenched by the addition of 1N HCl
  4. additionpoured into ethyl acetate (100 mL)
  5. washThe solution Was washed once with 1N HCl (100 mL)
  6. washThe 100 mL of 1N HCl wash
  7. extractionwas extracted With ethyl acetate (100 mL)
  8. washwashed With 1N HCl, water and brine
  9. customEvaporation of the solution in vacuo
  10. customresulted in a semi-solid residue
  11. temperatureheated on a steam bath for several minutes
  12. temperatureUpon cooling
  13. filtrationthe solidified product was collected by filtration
  14. customRecrystallization from ethanol (3A)

Sources & evidence

ORD record
ord-9d633578388845ff9d9209a87624f689
Source dataset
uspto-grants-1994_01
Patent number
US05281590

Reaction notes

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