Acetyl chloride → HCID 58521962, compound

HRID 2390283Notes

Reaction equation

HRID 2390283 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:9]([CH2:12][CH2:13][CH3:14])(=[O:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].CN1CC[O:19][CH2:18][CH2:17]1.C(Cl)(=O)C>C(Cl)Cl.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:9]([CH2:12][CH2:13][CH3:14])(=[O:11])=[O:10])=[C:6]([NH:7][C:18](=[O:19])[CH3:17])[CH:8]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 79724-MethylmorpholineHCID 43168856HCID 43168856, compound2×

Product 1

HCID 58521962HCID 58521962, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-methyl-2-(propylsulfonyl) aniline (Intermediate 228; 6.0 g, 28 mmol) in DCM (100 ml) was added N-methyl morpholine (4.3 g, 42.1 mmol) and Acetyl chloride (2.4 g, 31 mmol). The reaction mixture was stirred at RT for 12 h. The reaction mixture was diluted with water (200 ml), the organic layer was washed with brine solution and dried over sodium sulphate and evaporated. The crude product was purified by column chromatography (silica) using petroleum ether/ethyl acetate as eluent to afford the title compound (5.0 g, 70%) as a white solid.

Workup

  1. washthe organic layer was washed with brine solution
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe crude product was purified by column chromatography (silica)

Sources & evidence

ORD record
ord-5a566120f8ef4ee29bb305f70be0402e
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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