4-Iodoaniline → HCID 13537038, compound

HRID 981149Notes

Reaction equation

HRID 981149 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, compoundYield 67.8%

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 mixture was stirred at room temperature for 1 h, concentrated, and partitioned between 2 N hydrochloric acid (100 ml) and EA (100 ml). The organic layer was washed with 2 N hydrochloric acid, water and brine, dried and concentrated to a solid which was recrystallised from cyclohexane to give the title compound (10.5 g) m.p. 80°-81°.

Workup

  1. concentrationconcentrated
  2. custompartitioned between 2 N hydrochloric acid (100 ml) and EA (100 ml)
  3. washThe organic layer was washed with 2 N hydrochloric acid, water and brine
  4. customdried
  5. concentrationconcentrated to a solid which
  6. customwas recrystallised from cyclohexane

Sources & evidence

ORD record
ord-964fa6b350164f279fbb93c6b5ead230
Source dataset
uspto-grants-1991_02
Patent number
US04990505

Reaction notes

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