Ethanolamine → 2-[[5-Amino-2-[(2-hydroxyethyl)amino]phenyl]sulfonyl]ethanol

HRID 232234Notes

Reaction equation

HRID 232234 reaction equation
NC1C=CC=CC=1.[OH:8][CH2:9][CH2:10][S:11]([C:14]1[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:15]=1Cl)(=[O:13])=[O:12].[CH2:24]([CH2:26][NH2:27])[OH:25]>CO>[OH:8][CH2:9][CH2:10][S:11]([C:14]1[CH:19]=[C:18]([CH:17]=[CH:16][C:15]=1[NH:27][CH2:26][CH2:24][OH:25])[NH2:20])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 6115AnilineHCID 136286432-Chloro-5-nitrophenyl hydroxyethyl sulfone

Product 1

HCID 136286472-[[5-Amino-2-[(2-hydroxyethyl)amino]phenyl]sulfonyl]ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The aniline compound employed under (a) with the β-sulfatoethylsulfonyl group can be prepared, for example, as follows: 132.8 parts of 2-(β-hydroxyethylsulfonyl)-4-nitrochlorobenzene are added slowly to a solution of 76.5 parts of ethanolamine in 500 parts by volume of methanol at a temperature of 65° C., and the reaction batch is stirred for a further 6 hours at this temperature. 400 parts by volume of methanol are subsequently distilled off from the reaction batch while simultaneously and continuously adding water. 2-(β-hydroxyethylsulfonyl)-4-nitro-1-(β-hydroxyethyl)aminobenzene crystallizes on cooling from the now aqueous medium in high purity. This compound can be employed for the conversion of the nitro group to the amino group during catalytic hydrogenation. For this, 58 parts of this nitro compound are dissolved in 400 parts by volume of methanol and hydrogenated in an autoclave in the presence of a nickel catalyst at a temperature of 100° C. and pressure of 50 bar of hydrogen. The catalyst is subsequently filtered off and the filtrate allowed to crystallize out by cooling of the methanolic solution. 3-(β-hydroxyethylsulfonyl)-4-(β-hydroxyethylamino)aniline is obtained in good yield and high purity.

Workup

  1. distillation400 parts by volume of methanol are subsequently distilled off from the reaction batch while simultaneously and continuously adding water
  2. custom2-(β-hydroxyethylsulfonyl)-4-nitro-1-(β-hydroxyethyl)aminobenzene crystallizes
  3. temperatureon cooling from the now aqueous medium in high purity
  4. dissolutionFor this, 58 parts of this nitro compound are dissolved in 400 parts by volume of methanol
  5. customhydrogenated in an autoclave in the presence of a nickel catalyst at a temperature of 100° C. and pressure of 50 bar of hydrogen
  6. filtrationThe catalyst is subsequently filtered off
  7. customto crystallize out
  8. temperatureby cooling of the methanolic solution

Sources & evidence

ORD record
ord-5889ead722424ab8840479470c83973a
Source dataset
uspto-grants-1989_07
Patent number
US04851527

Reaction notes

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