Hydrochloric Acid → n-(3-((2-Chlorothiazol-5-yl)methyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene)nitramide
Reaction equation
[ClH:1].C(S[C:10]1[S:11][C:12]([CH2:15][N:16]2[C:21](=[N:22][N+:23]([O-:25])=[O:24])[N:20]([CH3:26])[CH2:19][O:18][CH2:17]2)=[CH:13][N:14]=1)C1C=CC=CC=1.ClCl>ClC1C=CC=CC=1>[Cl:1][C:10]1[S:11][C:12]([CH2:15][N:16]2[C:21](=[N:22][N+:23]([O-:25])=[O:24])[N:20]([CH3:26])[CH2:19][O:18][CH2:17]2)=[CH:13][N:14]=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 190 g of 3-(2-benzylthiothiazol-5-ylmethyl)-5-methyl-4 -nitroimino-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 120 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-6152fb99f56147cf82fe741dcf5cb063
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06211381B1
Reaction notes
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