Hydrochloric Acid → n-(3-((2-Chlorothiazol-5-yl)methyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene)nitramide
Reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:8][O:7][CH2:6][N:5]([CH2:9][C:10]2[S:14][C:13](SC3C=CC=CC=3)=[N:12][CH:11]=2)[C:4]1=[N:22][N+:23]([O-:25])=[O:24].ClCl>ClC1C=CC=CC=1>[Cl:1][C:13]1[S:14][C:10]([CH2:9][N:5]2[C:4](=[N:22][N+:23]([O-:25])=[O:24])[N:3]([CH3:2])[CH2:8][O:7][CH2:6]2)=[CH:11][N:12]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 300 g of aqueous hydrochloric acid (32%) and 150 g of chlorobenzene are added with stirring 183 g of 5-methyl-4-nitroimino-3-(2-phenylthiothiazol-5-ylmethyl)-perhydro-1,3,5-oxadiazine within 5 minutes. 124 g of chlorine are then passed into the mixture at 20 to 25° over a period of 4 hours. After stirring for a further 2 hours, the excess of chlorine is removed by introduction of nitrogen, and the aqueous phase (containing the title compound in hydrochloride form) is separated off and adjusted to pH 5 with aqueous sodium hydroxide solution (30%). The crystalline precipitate is filtered off, washed with water and dried at 50° in vacuo, yielding 132 g of the title compound (purity: 97%) melting at 132 to 135°.
Workup
- additionare added
- customthe excess of chlorine is removed by introduction of nitrogen
- additionthe aqueous phase (containing the title compound in hydrochloride form)
- customis separated off
- filtrationThe crystalline precipitate is filtered off
- washwashed with water
- customdried at 50° in vacuo
Sources & evidence
- ORD record
- ord-da928a7ad28b4cddb51df6dd53ee964a
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06211381B1
Reaction notes
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