Diethyl Ether → HCID 58896084, compound

HRID 269437Notes

Reaction equation

HRID 269437 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+].C(OCC)C>CN(C=O)C>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([N:11]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:13])=[O:14])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 11430Potassium CarbonateHCID 123691-BromoheptaneHCID 3675686HCID 3675686, compound

Product 1

HCID 58896084HCID 58896084, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-(3,5-Dimethoxy-phenyl)-4-methyl-benzenesulfonamide (15.0 g, 48.9 mmol), 1-bromoheptane (9.63 g, 53.8 mmol) and potassium carbonate (17.1 g, 124.2 mmol) in anhydrous DMF (100 mL) was stirred and heated at 120 ° C. for 4 h, and then cooled to room temperature and poured into ice-cold water (400 mL). Diethyl ether (400 mL) was added to extract the product. The ethereal solution was separated and washed with water, brine and dried with Na2SO4. Removal of solvent and drying reagent provided 19.50 g of light yellow liquid, which was treated with small amount of diethyl ether to give 19.10 g (96.4%) of the title compound as a white solid upon cooling.

Workup

  1. temperaturecooled to room temperature
  2. extractionto extract the product
  3. customThe ethereal solution was separated
  4. washwashed with water, brine
  5. dry with materialdried with Na2SO4
  6. customRemoval of solvent
  7. customdrying reagent
  8. customprovided 19.50 g of light yellow liquid, which

Sources & evidence

ORD record
ord-400b797965c54f07a82883d9219aa667
Source dataset
uspto-grants-2008_11
Patent number
US07446229B2

Reaction notes

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