O-Ethyl hydrazinecarbothioate → 5-(4-chloro-3-nitrophenyl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9](Br)[CH3:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[NH:16]([C:18](=[S:22])[O:19]CC)[NH2:17]>C(O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:10])[S:22][C:18](=[O:19])[NH:16][N:17]=2)=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14]Participants
5
Procedure
22 g (75 mM) of 1-(4-chloro-3-nitrophenyl)-2-bromopropan-1-one and 8 ml (75 mM) of O-ethyl hydrazinecarbothioate in 150 ml of ethanol are refluxed for 16 hours with stirring. The reaction medium is then concentrated under vacuum and the residue obtained is taken up in water. The aqueous phase is extracted twice with ethyl acetate and the combined organic phases are washed with water and then dried over anhydrous sodium sulfate. The solvent is evaporated off under vacuum to give an oil, which is purified on a column of silica using a dichloromethane/acetone mixture (95/5) as eluent. 5 g of 5-(4-chloro-3-nitrophenyl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one are obtained.
Workup
- concentrationThe reaction medium is then concentrated under vacuum
- customthe residue obtained
- extractionThe aqueous phase is extracted twice with ethyl acetate
- washthe combined organic phases are washed with water
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent is evaporated off under vacuum
- customto give an oil, which
- customis purified on a column of silica using a dichloromethane/acetone mixture (95/5) as eluent
Sources & evidence
- ORD record
- ord-83d492c719024386b4ad22f46642f1e6
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232272B2
Reaction notes
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