Ethanol → Indoaniline

HRID 2226340Notes

Reaction equation

HRID 2226340 reaction equation
[CH2:1]([OH:3])[CH3:2].CS([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1O)(=O)=O.O.[NH3:17]>O.[N+]([O-])([O-])=O.[Ag+]>[CH:11]1[C:10](=[N:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:17])=[CH:11][CH:10]=2)[CH:9]=[CH:14][C:1](=[O:3])[CH:2]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 316696N-(2-hydroxyphenyl)methanesulfonamideHCID 12896473Azane;hydrate

Product 1

HCID 24748760IndoanilineYield 76%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalyst2×HCID 962WaterSolvent2×

Procedure

150 ml of ethanol was added to 3.7 g of 2-methylsulfonylaminophenol of the following structural formula: ##STR108## and 5.24 g of a compound of the following structural formula: ##STR109## stirred at room temperature, and then a solution of 3.4 g of silver nitrate in 15 ml of water was added dropwise. 15 ml of a 28% ammonia water was added thereto, further a solution of 1.5 g of silver nitrate in 10 ml of water was added dropwise, and the reaction was effected at 30°-40° C. for 3 hours. After completion of the reaction, it was extracted with chloroform, the solvent was distilled off, and the residue was purified by column chromatography using chloroform to obtain 5.27 g (yield 76% based on the theoretical yield) of a purified product of an indoaniline type dye of the following structural formula: ##STR110## The dye thus obtained had a melting pont of 135°-137° C. and a maximum absorption wavelength (chloroform) of 640 nm.

Workup

  1. customAfter completion of the reaction, it
  2. extractionwas extracted with chloroform
  3. distillationthe solvent was distilled off
  4. customthe residue was purified by column chromatography
  5. customto obtain 5.27 g (yield 76%

Sources & evidence

ORD record
ord-780620cdeb574c4aa29f730ffcabea22
Source dataset
uspto-grants-1994_09
Patent number
USRE034737

Reaction notes

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