4-Toluenesulfonyl chloride → 1-Chloro-1,4-dicyano-3-thiabutane

HRID 465681Notes

Reaction equation

HRID 465681 reaction equation
[Cl:1][CH:2]([C:9]#[N:10])[CH2:3][S:4][CH2:5][C:6]([NH2:8])=O.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>Cl>[Cl:1][CH:2]([C:9]#[N:10])[CH2:3][S:4][CH2:5][C:6]#[N:8]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 109541055-Chloro-5-cyano-3-thiapentanamide

Product 1

HCID 109427521-Chloro-1,4-dicyano-3-thiabutane

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To the mixture obtained from Example 1, tosyl chloride (42 g) was added in portions with cooling. The resultant mixture was stirred for 5.5 hours, and then stood overnight. The solution was then poured into 4M hydrochloric acid (300 ml), stirred for 30 minutes, and then extracted with dichloromethane (×4). The combined extracts were washed with saturated brine, dried (magnesium sulphate) and evaporated to obtain the title compound as a dark red oil (30.95 g) 'H n.m.r. δ (CDCl3) 3.35(2H, d, J=7Hz, CH2CH), 3.55(2H,s,CH2CN), 4.77 (1H,t, J=7Hz, CH2CH).

Workup

  1. temperaturewith cooling
  2. extractionextracted with dichloromethane (×4)
  3. washThe combined extracts were washed with saturated brine
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated

Sources & evidence

ORD record
ord-98297fa024e548159c6e4a2148fa8f88
Source dataset
uspto-grants-1992_10
Patent number
US05153330

Reaction notes

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