N,N-Dimethylaniline → HCID 178429659, compound

HRID 1577148Notes

Reaction equation

HRID 1577148 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].S(=O)(=O)(O)O.Cl[C:22]1[NH:23][CH2:24][CH2:25][N:26]=1.O.CN(C)C1C=CC=CC=1>CO.ClCCl>[CH3:1][C:2]1[CH:8]=[C:7]([S:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:6]=[CH:5][C:3]=1[N:4]=[C:22]1[NH:26][CH2:25][CH2:24][NH:23]1

Participants

7

Reactant 4

HCID 949N,N-DimethylanilineHCID 962WaterHCID 105366492-Methyl-4-(phenylthio)benzenamineHCID 125033982-Chloroimidazoline sulfate

Product 1

HCID 178429659HCID 178429659, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The aniline derivative from Step C (3.0 g, 14 mmoles) is allowed to react with 2-chloro-2-imidazoline bisulfate (4.04 g, 20 mmoles) in methanol (60 ml) containing water (10 ml) and N,N-dimethylaniline (2.67 g, 22 mmoles). After 72 hours the reaction is worked up in the manner described in Example 2, except that the initial dichloromethane extracts are evaporated to a residue and triturated with hexane before extraction with 2 N acetic acid. The yield of pure product is 2.95 g, m.p. 140°-141° C.

Workup

  1. customare evaporated to a residue
  2. customtriturated with hexane before extraction with 2 N acetic acid

Sources & evidence

ORD record
ord-e560a1354e104d8db12ec27c8603ac09
Source dataset
uspto-grants-1981_09
Patent number
US04287201

Reaction notes

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