4-Chloroaniline → HCID 86745778, compound

HRID 1195924Notes

Reaction equation

HRID 1195924 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:9]([S:11]([F:14])(=[O:13])=[O:12])=[CH2:10]>CN(C=O)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:10]=[CH:9][S:11]([F:14])(=[O:13])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78124-Chloroaniline2×HCID 69612Ethenesulfonyl fluoride

Product 1

HCID 86745778HCID 86745778, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (50 mL) solution of 4-chloroaniline (3.0 g, 23.5 mmol) was added ethenesulfonyl fluoride (3.3 mL, 30 mmol). The solution was heated at 110° C. until the 4-chloroaniline was consumed (monitored by tlc). The orange solution was diluted with 1 liter of water and the resulting oily precipitate was extracted into ether. The combined organic layers was washed with water and brine and dried (MgSO4). After the ether had been removed by distillation, the brown residue afforded the title compound (4.56 g, 81%) as yellow needles which could be crystallized from ether/hexane, mp 61°-63° C. (lit. mp 62°-63° C.; Hoechst's German Patent 1104968).

Workup

  1. customwas consumed (monitored by tlc)
  2. additionThe orange solution was diluted with 1 liter of water
  3. extractionthe resulting oily precipitate was extracted into ether
  4. washThe combined organic layers was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customAfter the ether had been removed by distillation

Sources & evidence

ORD record
ord-ae4c6f048c2743549694c4e70bb99e8a
Source dataset
uspto-grants-1992_05
Patent number
US05112866

Reaction notes

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