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

HRID 44282

Reaction equation

HRID 44282 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:14][C:15]([NH:17][NH2:18])=[S:16])C>C(#N)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[CH2:2][S:16][C:15](=[O:14])[NH:17][N:18]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 68303p-Chlorophenacyl bromideHCID 12567113O-Ethyl hydrazinecarbothioate

Product 1

HCID 3294735-(4-Chlorophenyl)-3,6-dihydro-1,3,4-thiadiazin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-1-(4-chloro-phenyl)-ethanone (90.71 mmoles) and hydrazine-carbothioic acid O-ethyl ester (90.71 mmoles) in acetonitrile (84 ml) is stirred at ambient temperature for 3 hours. The solid formed is filtered off, washed with acetonitrile and ethyl ether and then dried in vacuo to yield the title product, which is used directly in the next Step.

Workup

  1. customThe solid formed
  2. filtrationis filtered off
  3. washwashed with acetonitrile and ethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1ac677b44aaf48988d0fdf72e6301e2f
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Linked notes

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