Dichloromethane → 2-Chloro-5-(phenylsulphonyl)aniline

HRID 374875Notes

Reaction equation

HRID 374875 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[Cl:19])([O-])=O.ClCCl>C(O)C>[Cl:19][C:5]1[C:4]([NH2:1])=[CH:9][C:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:11])=[O:12])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 5804891-Chloro-2-nitro-4-(phenylsulfonyl)benzene

Product 1

HCID 30207732-Chloro-5-(phenylsulphonyl)anilineYield 82.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

2-Nitro-4-(phenylsulfonyl)chlorobenzene (9.8 g) and stannous chloride dihydrate (33.5 g) were suspended in absolute ethanol (200 mL) and heated to 75° C. for 40 minutes. The solution was evaporated and the resulting material was cooled to 0° C. Water (100 mL) was added, and the pH was adjusted to 8.0 with aqueous sodium hydroxide. The resulting solids were removed by filtration and the aqueous filtrate was extracted with ethyl acetate. The combined ethyl acetate solutions were evaporated to give a brown solid. Chromatography, with dichloromethane as the eluent yielded the aniline as an orange solid (7.3 g); mp: 105°-107° C.; 250 MHz NMR: 5.96 (s,2), 7.02 (dd,1 J=8, 2), 7.34 (d,1, J=2), 7.41 (d,1, J=8), 7.61 (m,3), 7.88 (d,2, J=7); MS: m/z=268(M+1).

Workup

  1. customThe solution was evaporated
  2. temperaturethe resulting material was cooled to 0° C
  3. additionWater (100 mL) was added
  4. customThe resulting solids were removed by filtration
  5. extractionthe aqueous filtrate was extracted with ethyl acetate
  6. customThe combined ethyl acetate solutions were evaporated
  7. customto give a brown solid

Sources & evidence

ORD record
ord-b82f3e4454414af581996391e6285189
Source dataset
uspto-grants-1996_01
Patent number
US05482969

Reaction notes

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