Acetone → HCID 86693328, compound

HRID 575298Notes

Reaction equation

HRID 575298 reaction equation
Br[CH:2]1[CH2:8][O:7][C:6]2[CH:9]=[CH:10][C:11]([I:13])=[CH:12][C:5]=2[N:4]2[N:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:16]=[C:3]12.CC(C)=[O:24]>O.[N+]([O-])([O-])=O.[Ag+]>[OH:24][CH:2]1[CH2:8][O:7][C:6]2[CH:9]=[CH:10][C:11]([I:13])=[CH:12][C:5]=2[N:4]2[N:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:16]=[C:3]12

Participants

5

Reactant 2

HCID 180AcetoneHCID 86693329HCID 86693329, compound

Product 1

HCID 86693328HCID 86693328, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×

Procedure

Silver nitrate (0.3 g, 2.00 equiv) was added to a stirred solution of ethyl 4-bromo-9-iodo-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2-carboxylate (400 mg, 0.86 mmol, 1.00 equiv) in acetone (20 mL)/water (20 mL) was added. The resulting mixture was stirred for 12 hours at room temperature, diluted with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:3) to give 0.12 g (35%) of the titled compound as a white solid. LC-MS (ES, m/z) 401[M+H]+.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:3)

Sources & evidence

ORD record
ord-bbc6986232bf415ba7fb87c9d6710bb5
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

Loading…