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

HRID 241735

Reaction equation

HRID 241735 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-ac965aab873d4f019cf92ec011495b64
Source dataset
uspto-grants-2014_02
Patent number
US08653073B2

Linked notes

Loading…