Hydrochloric Acid → HCID 22406120, compound

HRID 1492733Notes

Reaction equation

HRID 1492733 reaction equation
[H-].[Na+].[CH:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.COCCOCCN(CCOCCOC)CCOCCOC.F[C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:34]=1[NH:42][S:43]([CH3:46])(=[O:45])=[O:44].Cl>ClC1C=CC=CC=1>[CH:3]1([O:9][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:34]=2[NH:42][S:43]([CH3:46])(=[O:44])=[O:45])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 4416401N-(2-fluoro-5-nitrophenyl)methanesulfonamide

Product 1

HCID 22406120HCID 22406120, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To 2000 ml of a chlorobenzene solution containing 52.8 g of 60% sodium hydride were successively added 128.0 g of cyclohexanol and 8 ml of tris[2-(2-methoxyethoxy)ethyl]amine at room temperature, and then after stirring for 30 minutes, 100.0 g of N-(2-fluoro-5-nitrophenyl)methanesulfonamide was added under ice cooling, followed by stirring for 19 hours. The reaction solution, after addition of 1500 ml of 3N hydrochloric acid, was extracted with dichloromethane, and the organic layer was successively washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the residue was recrystallized from ethanol to give 98.5 g of N-(2-cyclohexyloxy-5-nitrophenyl)methanesulfonamide as yellow plates.

Workup

  1. customat room temperature
  2. stirringby stirring for 19 hours
  3. extractionwas extracted with dichloromethane
  4. washthe organic layer was successively washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-a6a8be5a18954169b3e2d162e977ec2d
Source dataset
uspto-grants-1994_12
Patent number
US05374764

Reaction notes

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