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

HRID 1094002Notes

Reaction equation

HRID 1094002 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-dbba271263234862bc1b344fe6d78c36
Source dataset
uspto-grants-2012_03
Patent number
US08133889B2

Reaction notes

Loading…