Hydrochloric Acid → 4-((1-Fluoro-4-oxocyclohexyl)methoxy)-3-nitrobenzenesulfonamide

HRID 707044Notes

Reaction equation

HRID 707044 reaction equation
[F:1][C:2]1([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][C:19]=2[N+:28]([O-:30])=[O:29])[CH2:7][CH2:6][C:5]2(OC3C=CC=CC=3[O:8]2)[CH2:4][CH2:3]1.Cl.C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[F:1][C:2]1([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][C:19]=2[N+:28]([O-:30])=[O:29])[CH2:3][CH2:4][C:5](=[O:8])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 671271814-((4'-Fluorospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-yl)methoxy)-3-nitrobenzenesulfonamide

Product 1

HCID 671267644-((1-Fluoro-4-oxocyclohexyl)methoxy)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of EXAMPLE 363A (860 mg) in ethanol (30 mL) was added concentrated HCl (10 mL) and the mixture was stirred at 100° C. for 3 hours. The mixture was neutralized with solid Na2CO3 and extracted with dichloromethane (300 mL) and washed with aqueous NaHCO3, water, brine and dried over Na2SO4. Filtration and evaporation of the solvent gave the title compound.

Workup

  1. extractionextracted with dichloromethane (300 mL)
  2. washwashed with aqueous NaHCO3, water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-afcbb5c9c574449e9556236efaf17716
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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