2,2',4'-Trichloroacetophenone → HCID 178456953, compound

HRID 1105567Notes

Reaction equation

HRID 1105567 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.[CH2:13]([NH:16][C:17](=[S:20])[NH:18][NH2:19])[CH2:14][CH3:15]>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:20][C:17]([NH:16][CH2:13][CH2:14][CH3:15])=[N:18][N:19]=1

Participants

4

Reactant 2

HCID 202502,2',4'-TrichloroacetophenoneHCID 1810736Hydrazinecarbothioamide, N-propyl-

Product 1

HCID 178456953HCID 178456953, compoundYield 126%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.70 g (0.03 mole) of 2,4-dichlorophenacyl chloride and 3.99 g (0.03 mole) of 4-n-propyl-thiosemicarbazide are reacted in 150 ml of methanol under the conditions of Example 2. The concentrated product is crystallized and then recrystallized from methanol/ethyl acetate, to produce 6.4 g of 5-(2,4-dichlorophenyl)-N-propyl-6H-1,3,4-thiadiazin-2-amine monohydrochloride. m.p. 184°-185° C. The product is then dried at 65° C. under high vacuum.

Workup

  1. customThe concentrated product is crystallized
  2. customrecrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-c810be4599a9420188f63e90a8e8e368
Source dataset
uspto-grants-1982_01
Patent number
US04309426

Reaction notes

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