N,O-Dimethylhydroxylamine → HCID 62735316, compound

HRID 925072Notes

Reaction equation

HRID 925072 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.[CH3:12][NH:13][O:14][CH3:15].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([N:13]([O:14][CH3:15])[CH3:12])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 14232N,O-DimethylhydroxylamineHCID 74653(3-Bromophenyl)acetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 62735316HCID 62735316, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-(3-bromophenyl)acetic acid (4.4 g, 20.56 mmol) in N,N-dimethylformamide (125 ml) was successively added N,O-dimethylhydroxyamine (4.5 g, 46.26 mmol), triethylamine (10 ml), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (8.9 g, 46.26 mmol) and 1-hydroxybenzotriazole (6.24 g, 46.26 mmol). The reaction mixture was stirred at room temperature overnight, and partitioned between ethyl acetate and brine. The organic phase was washed with brine, and concentrated. The residue was purified by flash chromatography on silica gel (50% ethyl acetate in hexane) to provide the title compound. MS (DCI/NH3) m/z 258 (M+H)+.

Workup

  1. custompartitioned between ethyl acetate and brine
  2. washThe organic phase was washed with brine
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-395f33c1d7174b77876045c41e5fb6f5
Source dataset
uspto-grants-2016_03
Patent number
US09283222B2

Reaction notes

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