Hydrochloric Acid → HCID 178516818, compound

HRID 963482Notes

Reaction equation

HRID 963482 reaction equation
[OH-:1].[Na+].Cl.O[NH2:5].Br[CH2:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=O)=[O:9].Cl>C(O)C>[CH:19]1([C:17]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[NH:10][C:8](=[O:9])[CH2:7][N+:5]=2[O-:1])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 19081199HCID 19081199, compound

Product 1

HCID 178516818HCID 178516818, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
40 °C

Procedure

To a stirred 2.63N aqueous sodium hydroxide (40 ml) was added hydroxyamine hydrochloride (8.70 g) and ethanol (40 ml), and the mixture was heated at 40° C. To the heated mixture was added dropwise a solution of N-bromomethylcarbonyl-2-cyclohexylcarbonylaniline (5.25 g) in ethanol (30 ml) at the same temperature, and stirred for 20 hours under the same condition. To the mixture was dropwise conc. HCl (7.3 ml) at the same temperature and stirred for 1 hour. After cooling to the room temperature, the mixture was concentrated in vacuo. The residue was taken up with ethyl acetate and water. The organic layer was separated and dried over sodium sulfate. The organic layer was concentrated to give a crude product. The crude product was purified by column chromatography on silica gel with a mixture of ethyl acetate and chloroform. The desired fractions were combined and concentrated in vacuo to give 5-cyclohexy-2,3-dihydro-1H-1,4-benzodiazepin-2-one-4-oxide.

Workup

  1. stirringstirred for 1 hour
  2. temperatureAfter cooling to the room temperature
  3. concentrationthe mixture was concentrated in vacuo
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationThe organic layer was concentrated
  7. customto give a crude product
  8. customThe crude product was purified by column chromatography on silica gel with a mixture of ethyl acetate and chloroform
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-102f749c16e4461c973a420dc4376d94
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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