Diethyl Ether → 3-Amino-2-benzyl-5-(hydroxymethyl)benzene-1-sulfonamide

HRID 2082872Notes

Reaction equation

HRID 2082872 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[NH2:12][C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([S:30](=[O:33])(=[O:32])[NH2:31])[C:22]=1[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:16](OC)=[O:17].C(OCC)(=O)C>N1C=CC=CC=1.O>[NH2:12][C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([S:30](=[O:33])(=[O:32])[NH2:31])[C:22]=1[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:16][OH:17]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 20294631Methyl 3-amino-4-benzyl-5-sulfamoylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 536869293-Amino-2-benzyl-5-(hydroxymethyl)benzene-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a stirred mixture of lithium aluminium hydride (12 g) and dry diethyl ether (350 ml), a solution of methyl 3-amino-4-benzyl-5-sulfamylbenzoate (30 g) in dry pyridine (300 ml) is dropwise added during 1-1.5 hours. After additional stirring for 3 hours, the mixture is cooled and ethyl acetate (25 ml) followed by water (50 ml) are very cautiously added dropwise. After stirring for a further 30 minutes, the solids are collected by filtration and dried in air. The filter cake is treated with hot 4 N hydrochloric acid (about 500 ml) to dissolve inorganic material. After cooling 3-amino-4-benzyl-5-sulfamylbenzyl alcohol is collected by filtration and dried in air. After recrystallization from aqueous ethanol it is obtained with a melting point of 159°-161° C.

Workup

  1. temperaturethe mixture is cooled
  2. additionare very cautiously added dropwise
  3. stirringAfter stirring for a further 30 minutes
  4. filtrationthe solids are collected by filtration
  5. customdried in air
  6. additionThe filter cake is treated with hot 4 N hydrochloric acid (about 500 ml)
  7. dissolutionto dissolve inorganic material
  8. temperatureAfter cooling 3-amino-4-benzyl-5-sulfamylbenzyl alcohol
  9. filtrationis collected by filtration
  10. customdried in air
  11. customAfter recrystallization from aqueous ethanol it
  12. customis obtained with a melting point of 159°-161° C.

Sources & evidence

ORD record
ord-baea04da22db4f8cabc7e85726a31d2a
Source dataset
uspto-grants-1978_04
Patent number
US04082851

Reaction notes

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