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

HRID 1390048Notes

Reaction equation

HRID 1390048 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 additional 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
  2. temperaturethe mixture is 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-d2836dadc55c4b7bb35eecb9d9b34f85
Source dataset
uspto-grants-1981_01
Patent number
US04247550

Reaction notes

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