Water → 3-Amino-5-(hydroxymethyl)-2-phenoxybenzene-1-sulfonamide

HRID 2082870Notes

Reaction equation

HRID 2082870 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:9]=[C:10]([CH:16]=[C:17]([S:26](=[O:29])(=[O:28])[NH2:27])[C:18]=1[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:11](OCC)=[O:12].C(OCC)(=O)C.O>O1CCOCC1.C(O)(=O)C>[NH2:7][C:8]1[CH:9]=[C:10]([CH:16]=[C:17]([S:26](=[O:29])(=[O:28])[NH2:27])[C:18]=1[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:11][OH:12]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 20294607Ethyl 3-amino-4-phenoxy-5-sulfamoylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 540361913-Amino-5-(hydroxymethyl)-2-phenoxybenzene-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred mixture of lithium aluminium hydride (12.5 g) and dry dioxane (250 ml), a solution of ethyl 3-amino-4-phenoxy-5-sulfamylbenzoate (50 g) in dry dioxane (250 ml) is dropwise added at 90° C during about one hour. After additonal stirring and heating for 3 hours the mixture is cooled, and ethyl acetate (25 ml) followed by water (50 ml) and 4 N acetic acid (310 ml) are very cautiously added dropwise. The solvents are thereafter removed in vacuo, and the residue is extracted with ethyl acetate (1 liter). The insoluble inorganic material is removed by filtration, and the filtrate is washed with aqueous sodium hydrogen carbonate and with water, and is then dried in the presence of magnesium sulphate. After filtration, the solvent is removed in vacuo to yield crude 3-amino-4-phenoxy-5-sulfamylbenzyl alcohol. After recrystallization from aqueous ethanol it is obtained with a melting point of 170° C.

Workup

  1. temperatureheating for 3 hours the mixture
  2. temperatureis cooled
  3. additionare very cautiously added dropwise
  4. customThe solvents are thereafter removed in vacuo
  5. extractionthe residue is extracted with ethyl acetate (1 liter)
  6. customThe insoluble inorganic material is removed by filtration
  7. washthe filtrate is washed with aqueous sodium hydrogen carbonate and with water
  8. dry with materialis then dried in the presence of magnesium sulphate
  9. filtrationAfter filtration
  10. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-2ca56cadb9064ea5a99aad3bdb7da680
Source dataset
uspto-grants-1978_04
Patent number
US04082851

Reaction notes

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