Sulfuric Acid → 4-[(iodomethyl)sulfonyl]aniline

HRID 1390015Notes

Reaction equation

HRID 1390015 reaction equation
[I:1][CH2:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12]C(=O)C)=[CH:8][CH:7]=1)(=[O:5])=[O:4].S(=O)(=O)(O)O>>[I:1][CH2:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)(=[O:4])=[O:5]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 232640N-[4-(Iodomethanesulfonyl)phenyl]ethanimidic acid

Product 1

HCID 2704084-[(iodomethyl)sulfonyl]aniline

Procedure

A mixture of 63.7 g. of N-[p-(iodomethylsulfonyl)-phenyl]acetamide and 360 ml. of 5.5 N sulfuric acid is stirred and heated at reflux until all of the solid dissolves. After cooling, the crude, solid product separates; it is collected, washed with cold water and air-dried. After crystallization from methanol, 26 g. of p-(iodomethylsulfonyl)aniline is obtained; m.p. 169.5°-72° C.

Workup

  1. additionA mixture of 63.7 g
  2. temperatureheated
  3. temperatureat reflux until all of the solid
  4. dissolutiondissolves
  5. temperatureAfter cooling
  6. customit is collected
  7. washwashed with cold water
  8. customair-dried
  9. customAfter crystallization from methanol, 26 g

Sources & evidence

ORD record
ord-dc12fa82aa754a83839ff90790299337
Source dataset
uspto-grants-1981_01
Patent number
US04247559

Reaction notes

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