Hydrochloric Acid → HCID 14771332, compound

HRID 476739Notes

Reaction equation

HRID 476739 reaction equation
CO.[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[C:8]([O:17][CH:18]2[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]2)[CH:7]=1)([O-:5])=[O:4].[BH4-].[Na+].Cl>O1CCCC1>[OH:24][CH:21]1[CH2:22][CH2:23][CH:18]([O:17][C:8]2[CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:11]=[CH:10][C:9]=2[NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 14771331HCID 14771331, compound

Product 1

HCID 14771332HCID 14771332, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 8 ml of a mixture of methanol and tetrahydrofuran (1:2) containing 0.23 g of N-[4-nitro-2-(4-oxocyclohexyloxy)phenyl]methanesulfonamide obtained in Example 5 (2) was added 0.01 g of sodium borohydride under ice cooling, and the mixture was stirred for 20 minutes. To the reaction solution was a dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed, in turn, with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (eluent; n-hexane:dichloromethane:ethyl acetate=1:1:1) and then by recrystallization from dichloromethane-n-hexane to give 0.17 g of N-[2-(4-hydroxycyclohexyloxy)-4-nitrophenyl]methanesulfonamide.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed, in turn, with water
  3. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (eluent; n-hexane:dichloromethane:ethyl acetate=1:1:1)
  6. customby recrystallization from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-4900dc18b14847309309c32bc50690df
Source dataset
uspto-grants-1989_12
Patent number
US04885367

Reaction notes

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