Hydrochloric Acid → 5-Chloro-5-methoxycarbonyl-3-thiapentanenitrile

HRID 465684Notes

Reaction equation

HRID 465684 reaction equation
S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[Cl:12][CH:13]([C:20]([O:22][CH3:23])=[O:21])[CH2:14][S:15][CH2:16][C:17]([NH2:19])=O.Cl>N1C=CC=CC=1>[Cl:12][CH:13]([C:20]([O:22][CH3:23])=[O:21])[CH2:14][S:15][CH2:16][C:17]#[N:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 198754855-Chloro-5-methoxycarbonyl-3-thiapentanamide

Product 1

HCID 198754845-Chloro-5-methoxycarbonyl-3-thiapentanenitrileYield 81.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Tosyl chloride (18.82 g) was added in portions to a stirred solution of 5-chloro-5-methoxycarbonyl-3-thiapentanamide (19 g), in dry pyridine (95 ml). Heat was evolved during the addition. The mixture was stirred for 4 hours, stood overnight, and poured into 4M hydrochloric acid (400 ml) and extracted with dichloromethane. The combined extracts were washed with 4M hydrochloric acid (×3) and saturated brine, dried (magnesium sulphate) and evaporated to obtain the title compound as a dark red oil (14.2 g) 1H n.m.r. δ (CDCl3) 3.28 (2H,d, J=7Hz, CH2CH), 3.45 (2H, s, CH2CN), 3.83 (3H,s,CO2Me), 4.54 (1H,t, J=7Hz, CH2CH).

Workup

  1. temperatureHeat
  2. additionwas evolved during the addition
  3. waitstood overnight
  4. extractionextracted with dichloromethane
  5. washThe combined extracts were washed with 4M hydrochloric acid (×3) and saturated brine
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated

Sources & evidence

ORD record
ord-6d2f0f8bbb1b4f81b06c38f22f7c8b93
Source dataset
uspto-grants-1992_10
Patent number
US05153330

Reaction notes

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