Water → HCID 53669230, compound

HRID 1390049Notes

Reaction equation

HRID 1390049 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:9]=[C:10]([CH:16]=[C:17]([S:30](=[O:33])(=[O:32])[NH2:31])[C:18]=1[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)[C:11](OCC)=[O:12].C(OCC)(=O)C.O>COCCOC.C(O)(=O)C>[NH2:7][C:8]1[CH:9]=[C:10]([CH:16]=[C:17]([S:30](=[O:32])(=[O:33])[NH2:31])[C:18]=1[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:28])([F:27])[F:29])[CH:21]=1)[CH2:11][OH:12]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 20294539HCID 20294539, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 53669230HCID 53669230, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a stirred mixture of lithium aluminium hydride (5.0 g) and dry 1,2-dimethoxyethane (100 ml), a solution of ethyl 3-amino-4-(3'-trifluoromethylphenoxy)-5-sulfamylbenzoate (20 g) in dry 1,2-dimethoxyethane (100 ml) is dropwise added at 100° C. during about 1 hour. After additional stirring and heating for 3 hours, the mixture is cooled, and ethyl acetate (10 ml) followed by water (20 ml) and 4 N acetic acid (125 ml) are very cautiously added dropwise. The solvents are thereafter removed in vacuo and the residue is extracted with ethyl acetate (300 ml). 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-(3'trifluoromethylphenoxy)-5-sulfamylbenzyl alcohol. After recrystallization from diethyl ether/petroleum ether it is obtained with a melting point of 133°-134° 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 (300 ml)
  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-cd12215d72d24c1a9352f64865551022
Source dataset
uspto-grants-1981_01
Patent number
US04247550

Reaction notes

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