Aniline → HCID 178463276, compound

HRID 1606626Notes

Reaction equation

HRID 1606626 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:10]([NH:13][C:14](=[NH:16])[CH3:15])(=[O:12])=[O:11])[CH:6]=[C:7]([I:9])[CH:8]=1)#[N:2].N[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClC1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([S:10]([NH:13][C:14](=[N:16][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:15])(=[O:12])=[O:11])[CH:6]=[C:7]([I:9])[CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 6115AnilineHCID 178465675HCID 178465675, compound

Product 1

HCID 178463276HCID 178463276, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 367 mg. (1 mmole) of N-(3-cyano-5-iodophenylsulfonyl) acetamidine in 10 ml. of chlorobenzene is heated with 205 mg. (2.2 mmoles) of aniline and the reaction mixture heated to reflux for 3 hours. The reaction mixture is cooled in an ice bath and filtered to remove the precipitate of aniline hydrochloride. The filtrate is treated with hexane affording crystalline N-(3-cyano-5-iodophenylsulfonyl)-N'-phenyl acetamidine.

Workup

  1. temperatureto reflux for 3 hours
  2. temperatureThe reaction mixture is cooled in an ice bath
  3. filtrationfiltered
  4. customto remove the precipitate of aniline hydrochloride
  5. additionThe filtrate is treated with hexane affording crystalline N-(3-cyano-5-iodophenylsulfonyl)-N'-phenyl acetamidine

Sources & evidence

ORD record
ord-59c8309ea6b44b6d916f6888eceffa13
Source dataset
uspto-grants-1976_04
Patent number
US03953492

Reaction notes

Loading…