2-Chloro-4'-fluoroacetophenone → HCID 178463646, compound

HRID 1105560Notes

Reaction equation

HRID 1105560 reaction equation
[CH2:1]([NH:3][C:4](=[S:7])[NH:5][NH2:6])[CH3:2].[F:8][C:9]1[CH:18]=[CH:17][C:12]([C:13](=O)[CH2:14][Cl:15])=[CH:11][CH:10]=1>CO>[ClH:15].[CH2:1]([NH:3][C:4]1[S:7][CH2:14][C:13]([C:12]2[CH:17]=[CH:18][C:9]([F:8])=[CH:10][CH:11]=2)=[N:6][N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 1202482-Chloro-4'-fluoroacetophenoneHCID 15517804-Ethyl-3-thiosemicarbazide

Product 1

HCID 178463646HCID 178463646, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

11.19 g of 4-ethyl-thiosemicarbazide and 17.6 g of 4-fluorophenacyl chloride are heated and stirred under reflux (65° C.) in 400 ml of methanol for 30 minutes in a one liter round bottom flask equipped with a magnetic stirring bar and a condenser protected by a CaCl2 drying tube. The solution is allowed to cool to room temperature and is then concentrated to a yellow solid residue. The residue is recrystallized from methanol/butanone yielding 21.0 g (75.5%) of N-ethyl-5-(4-fluorophenyl)-6H-1,3,4-thiadiazin-2-amine hydrochloride. m.p. 192°-193° C. The fluffy, yellowish white solid is dried under high vacuum at 65° C.

Workup

  1. customequipped with a magnetic stirring bar and a condenser
  2. customprotected by a CaCl2 drying tube
  3. concentrationis then concentrated to a yellow solid residue
  4. customThe residue is recrystallized from methanol/butanone yielding 21.0 g (75.5%) of N-ethyl-5-(4-fluorophenyl)-6H-1,3,4-thiadiazin-2-amine hydrochloride
  5. customThe fluffy, yellowish white solid is dried under high vacuum at 65° C.

Sources & evidence

ORD record
ord-f7f5809eec8e4224b97c6167e769917c
Source dataset
uspto-grants-1982_01
Patent number
US04309426

Reaction notes

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