Water → HCID 53916225, compound

HRID 1903050Notes

Reaction equation

HRID 1903050 reaction equation
[CH3:1][N:2]([CH3:24])[S:3]([NH:6][C:7]1[CH:8]=[C:9]([CH:21]=[CH:22][CH:23]=1)[C:10](=[N:19][OH:20])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)(=[O:5])=[O:4].C(N(CC)CC)C.[C:32](Cl)(=[O:34])[CH3:33].O>C(Cl)Cl>[C:32]([O:20][N:19]=[C:10]([C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)[C:9]1[CH:21]=[CH:22][CH:23]=[C:7]([NH:6][S:3]([N:2]([CH3:1])[CH3:24])(=[O:5])=[O:4])[CH:8]=1)(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 73185421HCID 73185421, compound

Product 1

HCID 53916225HCID 53916225, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 3-[N-(dimethylaminosulfonyl)amino]-4'-methoxybenzophenone oxime (1.5 g) and triethylamine (650 mg) in dry methylene chloride (15 ml) is stirred under icy water cooling. A solution of acetyl chloride (337 mg) in dry methylene chloride (3 ml) is dropwise added to the suspension, and 30 minutes later the reaction mixture is mixed with icy water, washed with water, dried over anhydrous sodium sulfate and concentrated in vacuum. The residue is chromatographed on a column of Lobar Lichroprep Si 60, which is eluted with benzene:ethyl acetate (2:1). The eluates from the fraction No. 5-18 are combined and concentrated to give 3-[N-(dimethylaminosulfonyl)amino]-4'-methoxybenzophenone O-acetyloxime (500 mg) as an oil.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuum
  4. customThe residue is chromatographed on a column of Lobar Lichroprep Si 60, which
  5. washis eluted with benzene:ethyl acetate (2:1)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8117741beb7742588545b144b559bf6c
Source dataset
uspto-grants-1984_03
Patent number
US04435394

Reaction notes

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