p-Chlorophenacyl bromide → 5-(4-Chlorophenyl)-3,6-dihydro-1,3,4-thiadiazin-2-one

HRID 2087

Reaction equation

HRID 2087 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=O.C[O:13][C:14]([NH:16][NH2:17])=[S:15]>C(#N)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[CH2:2][S:15][C:14](=[O:13])[NH:16][N:17]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 68303p-Chlorophenacyl bromideHCID 10171237O-methyl hydrazinecarbothioate

Product 1

HCID 3294735-(4-Chlorophenyl)-3,6-dihydro-1,3,4-thiadiazin-2-oneYield 48.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-p-chloroacetophenone (9.16 g), methoxythiocarbonylhydrazine (13.0 g) and acetonitrile (75 ml) was refluxed overnight and then cooled and filtered. The light yellow solid was washed with hexane and dried yielding 5-(4-chlorophenyl)-3H,6H-1,3,4-thiadiazin-2-one (4.3 g).

Workup

  1. temperaturewas refluxed overnight
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe light yellow solid was washed with hexane
  5. customdried

Sources & evidence

ORD record
ord-be3327987e254f7c83d2e21521f5ed8d
Source dataset
uspto-grants-1998_03
Patent number
US05728694

Linked notes

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