Hydrochloric Acid → HCID 20360840, compound

HRID 1390047Notes

Reaction equation

HRID 1390047 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:14]1[C:24]([S:25](=[O:28])(=[O:27])[NH2:26])=[CH:23][C:17]([C:18](OCC)=[O:19])=[CH:16][C:15]=1[S:29][CH3:30])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OCC)(=O)C.Cl>C(OCC)C.O>[CH2:7]([C:14]1[C:24]([S:25](=[O:28])(=[O:27])[NH2:26])=[CH:23][C:17]([CH2:18][OH:19])=[CH:16][C:15]=1[S:29][CH3:30])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 20294579HCID 20294579, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20360840HCID 20360840, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred mixture of lithium aluminium hydride (24 g) and dry diethyl ether (500 ml), a solution of ethyl 4-benzyl-3-methylthio-5-sulfamylbenzoate (85 g) in dry diethyl ether (3 liters) is dropwise added during 1-1.5 hours. After additional stirring for 3 hours, the mixture is cooled, and ethyl acetate (60 ml) followed by water (100 ml) and 4 N hydrochloric acid (1 liter) are very cautiously added dropwise. The organic layer is separated, washed with 4 N hydrochloric acid and with water, and dried in the presence of magnesium sulphate. After filtration, the solvents are removed in vacuo to yield crude 4-benzyl-3-methylthio-5-sulfamylbenzyl alcohol. After recrystallization from ethanol it is obtained with a melting point of 190°-192° C.

Workup

  1. temperaturethe mixture is cooled
  2. additionare very cautiously added dropwise
  3. customThe organic layer is separated
  4. washwashed with 4 N hydrochloric acid and with water
  5. dry with materialdried in the presence of magnesium sulphate
  6. filtrationAfter filtration
  7. customthe solvents are removed in vacuo

Sources & evidence

ORD record
ord-6832a53e772f43b8bb1f18c25c3c47f5
Source dataset
uspto-grants-1981_01
Patent number
US04247550

Reaction notes

Loading…