p-Tolunitrile → Ethyl 5p-Tolyl-1,2,4-Thiadiazole-3-Carboxylate

HRID 1764059Notes

Reaction equation

HRID 1764059 reaction equation
O=C1[S:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])O1.[C:12]1([CH3:20])[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=1>>[C:12]1([CH3:20])[CH:17]=[CH:16][C:15]([C:18]2[S:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:19]=2)=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 7724p-TolunitrileHCID 12351252ethyl 2-oxo-2H-1,3,4-oxathiazole-5-carboxylate

Product 1

HCID 12351257Ethyl 5p-Tolyl-1,2,4-Thiadiazole-3-CarboxylateYield 41.5%

Procedure

A solution of 7.48 g (0.0427 mol) of ethyl 2-oxo-1,3,4-oxathiazole-5-carboxylate and 50.0 g (0.427 mol) of p-tolunitrile (redistilled) was held at 190° C for 72 hours. The reaction mixture, which contained the product in 16% yield, was concentrated under vacuum to 90° C (0.5 torr) to give 4.4 g of black residue. Elution chromatography of this material on 200 g of silica gel (Woelm, for dry column chromatography) with benzene gave 1.7 g of product. Crystallization of this material from hexane (charcoal) gave 0.72 g (7%) of solid, mp 65°-66.5° C.

Workup

  1. concentrationwas concentrated under vacuum to 90° C (0.5 torr)

Sources & evidence

ORD record
ord-00a1d7373e124ae791b607c13d01bea4
Source dataset
uspto-grants-1978_09
Patent number
US04115095

Reaction notes

Loading…