Ethanol → HCID 1379399, compound

HRID 2224618Notes

Reaction equation

HRID 2224618 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(O)C>N1C=CC=CC=1>[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][S:17]([C:14]1[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:16][CH:15]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 74014-Methoxybenzenesulfonyl chlorideHCID 119952-Iodoaniline

Product 1

HCID 1379399HCID 1379399, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2-iodoaniline (24.82 g, 113.3 mmol) in anhydrous pyridine (36 mL) was added 4-methoxybenzenesulfonyl chloride (23.42 g, 113.3 mmol). The dark solution was heated at 80° C. for one hour. The reaction mixture was evaporated in vacuo and the residue was poured onto an ice/water mixture. The aqueous phase was decanted and the oily residue was triturated several times with 150 mL portions of water. The resulting solid was collected by filtration and washed with water and hexane. The crude material was dried under a stream of air for three hours. Recrystallization from ethanol afforded tan crystals of the title compound (39.0 g, 81.71 mmol, 72% ). An analytically pure sample was prepared by recrystallization from acetone.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. additionthe residue was poured onto an ice/water mixture
  3. customThe aqueous phase was decanted
  4. customthe oily residue was triturated several times with 150 mL portions of water
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with water and hexane
  7. dry with materialThe crude material was dried under a stream of air for three hours

Sources & evidence

ORD record
ord-1cf59c78dee64d6987be70af2432f7c4
Source dataset
uspto-grants-2008_05
Patent number
US07378427B2

Reaction notes

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