Thionyl Chloride → 4-(4-Chloro-2-methylphenyl)-1,2,3-thiadiazole

HRID 857796Notes

Reaction equation

HRID 857796 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:10]/[NH:11]C(OCC)=O)/[CH3:9])=[C:4]([CH3:17])[CH:3]=1.[S:18](Cl)(Cl)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:10]=[N:11][S:18][CH:9]=2)=[C:4]([CH3:17])[CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 145779288ethyl N-[(E)-1-(4-chloro-2-methylphenyl)ethylideneamino]carbamate

Product 1

HCID 218661604-(4-Chloro-2-methylphenyl)-1,2,3-thiadiazole

Procedure

Ethyl (2E)-2-[1-(4-chloro-2-methylphenyl)ethylidene]hydrazine carboxylate (0.63 g, 2.45 mmol) was stirred with thionyl chloride (1 mL, 13.70 mmol) at 60° C. for 1 h. The mixture was cooled to room temperature and concentrated in vacuo. 4-(4-Chloro-2-methylphenyl)-1,2,3-thiadiazole was obtained as a red solid. MS m/z=211.5; 1H NMR (CDCl3, 400 MHz) δ 2.45 (s, 3H), 7.31 (dd, J=2.2, 8.2 Hz, 1H), 7.36 (d, J=1.8 Hz, 1H), 7.60 (d, J=8.2 Hz, 1H), 8.51 (s, 1H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5985d49596974f968ae550e062733b47
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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