Hydrochloric Acid → 4-(4-Acetamidophenylsulphonyl)-2-chloroaniline

HRID 2301054Notes

Reaction equation

HRID 2301054 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([Cl:23])[CH:15]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].O.Cl>[Fe].C(O)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([Cl:23])[CH:15]=2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 222874964-(4-Acetamidophenyl-sulphonyl)-2-chloro-nitrobenzene

Product 1

HCID 222873434-(4-Acetamidophenylsulphonyl)-2-chloroanilineYield 1,304.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron powder (2.5 g) was added to a stirred mixture of 4-(4-acetamidophenyl-sulphonyl)-2-chloro-nitrobenzene (Method 13) (0.67 g), water (2 ml), concentrated hydrochloric acid (0.5 ml) and ethanol (10 ml). The mixture was heated under reflux for 1 hour then evaporated to near dryness and partitioned between ethyl acetate and water. The organic layer was separated the aqueous layer was extracted with ethyl acetate (3×15 ml). The organic extracts were combined and dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 0-2% methanol/DCM to give the title compound (0.1 8 g) as a solid. NMR: 2.05 (s, 3H), 6.4 (s, 2H), 6.8 (d, 1H), 7.5 (d, 1H), 7.6 (d, 1H), 7.8 (q, 4H), 10.3 (brs, 1H); MS (ESP−): 323.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customthen evaporated
  4. custompartitioned between ethyl acetate and water
  5. customThe organic layer was separated the aqueous layer
  6. extractionwas extracted with ethyl acetate (3×15 ml)
  7. customdried
  8. customVolatile material was removed by evaporation
  9. customthe residue was purified by chromatography on a silica gel Mega Bond Elut column
  10. washeluting with 0-2% methanol/DCM

Sources & evidence

ORD record
ord-04d2986a3af54170aeda21a44a4b578d
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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