Water → (R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]-4-methylbenzenesulfonamide

HRID 2302086Notes

Reaction equation

HRID 2302086 reaction equation
[Li].[Cl:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH2:8][C@H:9]([NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:10][CH3:11].O>CO>[Cl:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH2:8][C@H:9]([NH:12][S:13]([C:16]1[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=1)(=[O:15])=[O:14])[CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 962WaterHCID 69848256(R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]-4-methylbenzenesulfonamide lithium salt

Product 1

HCID 11002430(R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]-4-methylbenzenesulfonamideYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 50.0 g (0.143 mol) of (R)-N-[1-[(3-chlorothien-2-yl )methyl]propyl]-4-methylbenzenesulfonamide lithium salt, prepared as described in PCT/US97/15729, in 50 g methanol is heated with stirring at 65° C. until dissolution of the solids is completed. The solution is cooled to 60° C. and 85 g water is added to the mixture dropwise. The mixture is stirred for 1.5 hours and then cooled to 20° C. The solids are isolated by filtration. Drying under vacuum with nitrogen bleed affords 46.6 g (95%) of the free base (R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]-4-methylbenzenesulfonamide.

Workup

  1. customprepared
  2. temperatureis heated
  3. temperatureThe solution is cooled to 60° C.
  4. stirringThe mixture is stirred for 1.5 hours
  5. temperaturecooled to 20° C
  6. customThe solids are isolated by filtration
  7. customDrying under vacuum with nitrogen

Sources & evidence

ORD record
ord-558184f185874d8ca70ae827d7e11278
Source dataset
uspto-grants-2002_08
Patent number
US06429315B1

Reaction notes

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