Methyl p-toluenesulfonate → HCID 20201050, compound

HRID 1381335Notes

Reaction equation

HRID 1381335 reaction equation
[O:1]=[C:2]1[C:6]2[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=3)=[N:8][C:9](=O)[C:5]=2[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)=[N:3]1.[C:25](=[O:28])([O-])[O-].[K+].[K+].[C:31]1(C)C=CC(S(OC)(=O)=O)=CC=1.[N+](C1C=CC=CC=1)([O-])=O>>[O:1]=[C:2]1[C:6]2=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=3)[N:8]([CH3:9])[C:25](=[O:28])[C:5]2=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)[N:3]1[CH3:31]

Participants

5

Reactant 4

HCID 6645Methyl p-toluenesulfonateHCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 22061442HCID 22061442, compound

Product 1

HCID 20201050HCID 20201050, compound

Procedure

9.5 parts of 1,4-diketo-3,6-di-(3'-methylphenyl)pyrrolo-[3,4-c]pyrrole, 9 parts of anhydrous potassium carbonate and 24 parts of methyl p-toluenesulfonate are heated at 190° C. with 85 parts of nitrobenzene for 1 hour, with stirring. The cooled reaction mixture is filtered. The dye formed remains dissolved in the solvent. The nitrobenzene is removed by means of steam distillation and the crude dye is purified by crystallisation from 45 parts of toluene. 3.8 parts of 1,4-diketo-2,5-dimethyl-3,6-di-(3'-methylphenyl)pyrrolo-[3,4-c]-pyrrole are obtained in the form of orange crystals of melting point 195°-197° C. (formula XIII). The dye gives a pure yellow shade of good fastness properties on PES by the method described in Example 1b. ##STR17##

Workup

  1. customThe cooled reaction mixture
  2. filtrationis filtered
  3. customThe dye formed
  4. dissolutionremains dissolved in the solvent
  5. customThe nitrobenzene is removed by means of steam distillation
  6. customthe crude dye is purified by crystallisation from 45 parts of toluene

Sources & evidence

ORD record
ord-b9ea9a07c8f84294b3e1db749f6a23ba
Source dataset
uspto-grants-1986_04
Patent number
US04585878

Reaction notes

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