2,2',4'-Trichloroacetophenone → HCID 12923148, compound

HRID 1105561Notes

Reaction equation

HRID 1105561 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4](=O)[CH2:5]Cl.[NH2:13][NH:14][C:15]([NH2:17])=[S:16]>CO>[ClH:1].[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]1[CH2:5][S:16][C:15]([NH2:17])=[N:14][N:13]=1

Participants

4

Reactant 2

HCID 202502,2',4'-TrichloroacetophenoneHCID 2723789Thiosemicarbazide

Product 1

HCID 12923148HCID 12923148, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

11.17 g (0.05 mole) of 2,4-dichlorophenacyl chloride and 4.36 g (0.05 mole) of thiosemicarbazide are stirred and heated in 250 ml of methanol at reflux (65° C.) for 30 minutes. The resultant suspension is allowed to cool and is filtered to yield a first crop of 4.56 g of 5-(2,4-dichlorophenyl)-6H-1,3,4-thiadiazin-2-amine hydrochloride. The reaction mixture is then diluted with ethyl acetate and concentrated on a steam bath further yielding 6.2 g of the same compound. The two products are added together and recrystallized from methanol/ethyl acetate. m.p. 170°-172° C.

Workup

  1. temperatureto cool
  2. filtrationis filtered

Sources & evidence

ORD record
ord-fbd4fc0ee90b456c95d362b18002dedf
Source dataset
uspto-grants-1982_01
Patent number
US04309426

Reaction notes

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