Thionyl Chloride → 5-(4-Methoxyphenyl)-4-phenyl-1,2,3-thiadiazole

HRID 2372360Notes

Reaction equation

HRID 2372360 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[N:17][NH:18]C(OCC)=O)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.O=[S:25](Cl)Cl>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:25][N:18]=[N:17][C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 54026400Ethyl [2-(4-methoxyphenyl)-1-phenylethylidene]hydrazine carboxylate

Product 1

HCID 134271805-(4-Methoxyphenyl)-4-phenyl-1,2,3-thiadiazoleYield 82.3%

Conditions

Temperature
60 °C

Procedure

The acylhydrazone 9 (4.6 g, 14.8 mol), was added to SOCl2 (25 ml) at 0° C. The reaction was stirred to 60° C. and was complete (by TLC) after 1.5 hour. SOCl2 was evaporated under reduced pressure and the crude oil was chromatographed on SiO2 (150 g), eluting with CH2Cl2 to afford 8 (3.25 g, 82.3%), m.p. 56.5°-58° C.

Workup

  1. customafter 1.5 hour
  2. customSOCl2 was evaporated under reduced pressure
  3. customthe crude oil was chromatographed on SiO2 (150 g)
  4. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-4e2841d8e3384d26ad368560fb698d57
Source dataset
uspto-grants-1992_03
Patent number
US05098918

Reaction notes

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