Dimethyl Disulfide → 5-(Methylthio)-2,4-Diaminotoluene

HRID 1982194Notes

Reaction equation

HRID 1982194 reaction equation
CSSC.CSC1C(N)=C(C)C=CC=1N.[CH3:16][S:17][C:18]1[C:19]([NH2:28])=[C:20](SC)[C:21]([NH2:25])=[C:22]([CH3:24])[CH:23]=1>>[CH3:16][S:17][C:18]1[C:19]([NH2:28])=[CH:20][C:21]([NH2:25])=[C:22]([CH3:24])[CH:23]=1

Participants

4

Reactant 3

HCID 12232Dimethyl DisulfideHCID 112643714-Methyl-2,6-bis(methylsulfanyl)benzene-1,3-diamineHCID 15919498Mono(methylthio)-2,4-diaminotoluene

Product 1

HCID 194374535-(Methylthio)-2,4-Diaminotoluene

Procedure

This example demonstrates preparation of a chain extender having the inventive aromatic diamine as a minor proportion. The reaction time was shorter. A sample was prepared using a single equivalent of methyl disulfide (95.4 g) under similar reaction conditions and the reaction was completed in 16 hours. The product was predominantly mono(methylthio)-2,4-diaminotoluene containing a minority portion of di(methylthio)-2,4-diaminotoluene. A distilled fraction (b.p. 156-161 @ 1.0 mm) had the following analysis:

Workup

  1. custompreparation of a chain extender
  2. customA sample was prepared
  3. customunder similar reaction conditions

Sources & evidence

ORD record
ord-93316cdc52ed492585841066516eb15d
Source dataset
uspto-grants-1986_06
Patent number
US04595742

Reaction notes

Loading…