HCID 58625117, compound → N-[3-(3-Formyl-4-nitro-phenylsulfanyl)-phenyl]-benzenesulfonamide

HRID 390226Notes

Reaction equation

HRID 390226 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:5]=[C:6]([S:13][C:14]2[CH:15]=[C:16]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]>Cl.C1COCC1.O>[CH:3]([C:4]1[CH:5]=[C:6]([S:13][C:14]2[CH:15]=[C:16]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])=[O:2]

Participants

5

Reactant 1

HCID 58625117HCID 58625117, compound

Product 1

HCID 58625048N-[3-(3-Formyl-4-nitro-phenylsulfanyl)-phenyl]-benzenesulfonamide

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-[3-(3-dimethoxymethyl-4-nitro-phenylsulfanyl)-phenyl]-benzenesulfonamide (0.027 mol) in 12N HCl (25 mL), THF (75 mL) and water (50 mL) was stirred overnight at room temperature, and then the mixture was extracted with ethyl acetate. The extract was washed with water and with a saturated aqueous Na2CO3 solution. The solvent was evaporated and the residue was purified by column chromatography over silica gel (eluent: CH2Cl2). The product fractions were collected and the solvent evaporated to yield the title compound as a residue.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and with a saturated aqueous Na2CO3 solution
  3. customThe solvent was evaporated
  4. customthe residue was purified by column chromatography over silica gel (eluent: CH2Cl2)
  5. customThe product fractions were collected
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-4a03216cb7d447619f350d5d501925bb
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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