Dimethylformamide → HCID 57901827, compound

HRID 1851363Notes

Reaction equation

HRID 1851363 reaction equation
[CH3:1][O:2][CH2:3][N:4]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[N:20]([CH2:22][O:23][CH3:24])[C:19]([C:25]1[N:29]=[CH:28][NH:27][N:26]=1)=[CH:18]2)[S:5]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)(=[O:7])=[O:6].CI.[C:32](=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:1][O:2][CH2:3][N:4]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[N:20]([CH2:22][O:23][CH3:24])[C:19]([C:25]1[N:26]([CH3:32])[N:27]=[CH:28][N:29]=1)=[CH:18]2)[S:5]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)(=[O:7])=[O:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178496779HCID 178496779, compound

Product 1

HCID 57901827HCID 57901827, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(methoxymethyl)-N-[1-(methoxymethyl)-2-(1H-1,2,4-triazol-3-yl)-1H-indol-7-yl]thiophene-2-sulfonamide (0.70 g), methyl iodide (0.20 mL), potassium carbonate (0.25 g) and N,N-dimethylformamide (8 mL) was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography and the title compound (0.14 g, yield 19%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:4-1:0, volume ratio). melting point 110-111° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2ad08d9560fa413eaa31bf63e5b23154
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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