4-Iodoaniline → HCID 13537038, compound

HRID 568870Notes

Reaction equation

HRID 568870 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-8d79628d6c214b9ab9c974bf0bf11a65
Source dataset
uspto-grants-1988_03
Patent number
US04730008

Reaction notes

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