Ethanone, 2-chloro-1,2-diphenyl- → 2-(3,4-Methylenedioxyphenyl)-4,5-diphenylthiazole

HRID 2049275

Reaction equation

HRID 2049275 reaction equation
[C:1]([NH2:12])(=[S:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.[C:13]1([C:19]([CH:21](Cl)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[CH2:6]1[O:7][C:8]2[CH:9]=[CH:10][C:2]([C:1]3[S:11][C:19]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:12]=3)=[CH:3][C:4]=2[O:5]1

Participants

4

Reactant 2

HCID 95343Ethanone, 2-chloro-1,2-diphenyl-HCID 27761262H-1,3-benzodioxole-5-carbothioamide

Product 1

HCID 203449832-(3,4-Methylenedioxyphenyl)-4,5-diphenylthiazoleYield 67.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiopiperonylamide (18.1 g, 0.10 mole) and desyl chloride (23.1 g, 0.10 mole) are heated under reflux in 95% ethanol (100 ml) for two hours. An oil precipitates which solidifies when the reaction mixture is cooled. The solid is collected and recrystallized from ethanolethyl acetate to give 24.0 g (67% yield ) of 2-(3,4-methylenedioxyphenyl)-4,5-diphenylthiazole, m.p. 121°-124° C. Thiopiperonylamide is also prepared from the corresponding nitrile by the method of Fairfull et al., J. Chem. Soc. 1952, 742.

Workup

  1. customAn oil precipitates which
  2. temperatureis cooled
  3. customThe solid is collected
  4. customrecrystallized from ethanolethyl acetate

Sources & evidence

ORD record
ord-52f6e35e790d48d48e59f5d026142358
Source dataset
uspto-grants-1980_04
Patent number
US04197306

Linked notes

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