Water → N-[3-(3-Formyl-4-nitro-phenylsulfanyl)-phenyl]-benzenesulfonamide

HRID 2088847Notes

Reaction equation

HRID 2088847 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].O>Cl.C1COCC1>[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 2

HCID 962WaterHCID 58625117HCID 58625117, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-[3-(3-dimethoxymethyl-4-nitro-phenylsulfanyl)-phenyl]-benzenesulfonamide (0.027 mol) in 12 N HCl (25 mL), THF (75 mL), and water (50 mL) was stirred overnight at room temperature, and then the mixture was extracted with EtOAc. The extract was washed with H2O and then with a saturated 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 was evaporated to yield the title compound as a residue.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe extract was washed with H2O
  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 was evaporated

Sources & evidence

ORD record
ord-3e3bee84181c44539841ba58dbb497c1
Source dataset
uspto-grants-2013_05
Patent number
US08436006B2

Reaction notes

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