4-Toluenesulfonyl chloride → 5-Chloro-5-methoxycarbonyl-3-thiapentanenitrile

HRID 465683Notes

Reaction equation

HRID 465683 reaction equation
[Cl:1][CH:2]([C:9]([O:11][CH3:12])=[O:10])[CH2:3][S:4][CH2:5][C:6]([NH2:8])=O.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>O>[Cl:1][CH:2]([C:9]([O:11][CH3:12])=[O:10])[CH2:3][S:4][CH2:5][C:6]#[N:8]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 198754855-Chloro-5-methoxycarbonyl-3-thiapentanamide

Product 1

HCID 198754845-Chloro-5-methoxycarbonyl-3-thiapentanenitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the mixture obtained from Example 4, tosyl chloride (39.34 g) was added in portions with vigorous stirring and heat was evolved. The mixture was stirred for 9.5 hours, stood overnight, then poured into water (500 ml), and extracted with dichloromethane. The combined extracts were washed with water (×2) and saturated brine, dried (magnesium sulphate) and evaporated to yield the title compound as a dark red oil (27.05 g).

Workup

  1. temperatureheat
  2. stirringThe mixture was stirred for 9.5 hours
  3. extractionextracted with dichloromethane
  4. washThe combined extracts were washed with water (×2) and saturated brine
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated

Sources & evidence

ORD record
ord-6956bbdfc3bf4f0c9a1352b595c6dead
Source dataset
uspto-grants-1992_10
Patent number
US05153330

Reaction notes

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