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

HRID 841191Notes

Reaction equation

HRID 841191 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([Cl:20])[CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.Cl>[Fe].C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([Cl:20])[CH:12]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 226212524-(4-Bromophenylsulphonyl)-2-chloro-nitrobenzene

Product 1

HCID 226212634-(4-Bromophenylsulphonyl)-2-chloroaniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron powder (2.5 g) was added to a stirred mixture of 4-(4-bromophenylsulphonyl)-2-chloro-nitrobenzene (Method 13) (0.6 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) and 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 0-25% ethyl acetate/hexane followed by trituration with ether to give the title compounde (0.11 g) as a solid. NMR: 6.42 (s, 2H), 6.82 (d, 1H), 7.5 (d, 1H), 7.8 (m, 5H); MS: 346 (M−H)−.

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
  6. extractionthe aqueous layer was 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 0-25% ethyl acetate/hexane
  11. customto give the title compounde (0.11 g) as a solid

Sources & evidence

ORD record
ord-583f17ad020b4df8bf83122e220cbb8d
Source dataset
uspto-grants-2002_04
Patent number
US06369273B1

Reaction notes

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