Acetyl chloride → HCID 49780328, compound

HRID 402301Notes

Reaction equation

HRID 402301 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]3[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=3)=[CH:19][CH:20]=2)[C:15]([CH2:29][NH2:30])=[CH:14]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(N(CC)CC)C>C1COCC1>[CH2:5]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]3[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=3)=[CH:19][CH:20]=2)[C:15]([CH2:29][NH:30][C:1](=[O:3])[CH3:2])=[CH:14]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 49783189HCID 49783189, compound

Product 1

HCID 49780328HCID 49780328, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (44 μl, 0.434 mmol) was added to a solution of (1-octyl-5-m-tolyl-1H-indol-3-yl)methanamine (220 mg, 0.628 mmol) and triethylamine (131 μl, 0.651 mmol) in THF (4 mL) at 0° C. The reaction mixture was allowed to stir at room temp for 60 min, the precipitate formed was filtered off, the filtrate was concentrated, and the residue was subjected to column chromatography (silica gel, CH2Cl2) to give sulphonamide 23 in 65% yield.

Workup

  1. customthe precipitate formed
  2. filtrationwas filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b3cbdda21ce44d9bbe95c391865336dc
Source dataset
uspto-grants-2014_06
Patent number
US08742100B2

Reaction notes

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