4-Iodoaniline → HCID 13537038, compound

HRID 1721897Notes

Reaction equation

HRID 1721897 reaction equation
[CH2:1]([S:5](Cl)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[I:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1>N1C=CC=CC=1>[I:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:5]([CH2:1][CH2:2][CH2:3][CH3:4])(=[O:7])=[O:6])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 108934-IodoanilineHCID 754301-Butanesulfonyl chloride

Product 1

HCID 13537038HCID 13537038, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Butanesulphonyl chloride (7.8 g) was added dropwise to a stirred solution of 4-iodobenzeneamine (10 g) in pyridine (50 ml) at 0°. The bright red mixture was stirred at room temperature for 1 h, then concentrated to an oil which was partitioned between 2N hydrochloric acid (100 ml) and EA (100 ml). The organic layer was washed with 2N hydrochloric acid, water and brine, dried (MgSO4) and concentrated to a pale brown solid which was recrystallised from CX to give the title compound as white flakes (10.5 g) m.p. 80°-81°.

Workup

  1. concentrationconcentrated to an oil which
  2. customwas partitioned between 2N hydrochloric acid (100 ml) and EA (100 ml)
  3. washThe organic layer was washed with 2N hydrochloric acid, water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to a pale brown solid which
  6. customwas recrystallised from CX

Sources & evidence

ORD record
ord-f12003063e664dd8bb4cdf24f317c3f3
Source dataset
uspto-grants-1989_08
Patent number
US04853382

Reaction notes

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