Thionyl Chloride → 4-o-Tolyl-[1,2,3]thiadiazole

HRID 857694Notes

Reaction equation

HRID 857694 reaction equation
[S:1](Cl)(Cl)=O.C(OC([NH:10][N:11]=[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])[CH3:13])=O)C>>[C:15]1([CH3:20])[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:12]1[N:11]=[N:10][S:1][CH:13]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 72765635N'-(1-o-tolyl-ethylidene)-hydrazinecarboxylic acid ethyl ester

Product 1

HCID 112753384-o-Tolyl-[1,2,3]thiadiazole

Conditions

Temperature
60 °C

Procedure

To thionyl chloride (1 ml), cooled to 0° C. was added N′-(1-o-tolyl-ethylidene)-hydrazinecarboxylic acid ethyl ester. The reaction mixture was heated to 60° C. for 1 h. Solvent evaporation gave 4-o-tolyl-[1,2,3]thiadiazole; 1 H NMR (CDCl3, 400 MHz) δ 8.51 (s, 1H), 7.65 (d, 1H, J=7.3 Hz), 7.36 (m, 3H), 2.46 (s, 3H).

Workup

  1. customSolvent evaporation

Sources & evidence

ORD record
ord-4dc6736e7aac47df84a27eb29b8010eb
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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