Methyl iodide → HCID 54093951, compound

HRID 1090183Notes

Reaction equation

HRID 1090183 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:8]([CH:9]=[CH:10][C:11]([CH:15]([CH3:17])[CH3:16])=[CH:12][CH:13]=2)=[C:7]([CH2:18][CH2:19][CH2:20][CH2:21][NH:22][S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:6]=1)=[O:4].[CH3:32]I.[Na]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:8]([CH:9]=[CH:10][C:11]([CH:15]([CH3:17])[CH3:16])=[CH:12][CH:13]=2)=[C:7]([CH2:18][CH2:19][CH2:20][CH2:21][N:22]([S:23]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)(=[O:24])=[O:25])[CH3:32])[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5360545SodiumHCID 10026206HCID 10026206, compound

Product 1

HCID 54093951HCID 54093951, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 6-Isopropyl-3-[4-(benzenesulfonylamino)butyl]-azulene-1-carboxylic acid methyl ester (0.50 g) in DMF (10 ml) was added to the suspension, and the mixture was stirred at 0° C. for 10 min. Then, methyl iodide (5 ml) was dropped into the solution of the sodium salt, and the mixture was stirred at the same temperature for 30 min. The reaction was quenched by the addition of saturated aqueous NH4Cl, followed by extraction with ethyl acetate. The combined ethyl acetate extracts were washed with water and brine, and dried over MgSO4. Removal of the solvent and the purification by silica gel column chromatography (ethyl acetate-n-hexane, 1:1) afforded the sulfonamide (0.51 g 99%) as a violet oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for 30 min
  2. customThe reaction was quenched by the addition of saturated aqueous NH4Cl
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with water and brine
  5. dry with materialdried over MgSO4
  6. customRemoval of the solvent
  7. customthe purification by silica gel column chromatography (ethyl acetate-n-hexane, 1:1)

Sources & evidence

ORD record
ord-39041cfe20e74c6d9b0ca394ec2830e4
Source dataset
uspto-grants-1992_01
Patent number
US05081152

Reaction notes

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