Hydrochloric Acid → n-(3-((2-Chlorothiazol-5-yl)methyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene)nitramide

HRID 1839853Notes

Reaction equation

HRID 1839853 reaction equation
C1(S[C:8]2[S:9][C:10]([CH2:13][N:14]3[C:19](=[N:20][N+:21]([O-:23])=[O:22])[N:18]([CH3:24])[CH2:17][O:16][CH2:15]3)=[CH:11][N:12]=2)C=CC=CC=1.[ClH:25].ClCl>ClC1C=CC=CC=1>[Cl:25][C:8]1[S:9][C:10]([CH2:13][N:14]2[C:19](=[N:20][N+:21]([O-:23])=[O:22])[N:18]([CH3:24])[CH2:17][O:16][CH2:15]2)=[CH:11][N:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24526ChlorineHCID 537725884H-1,3,5-Oxadiazin-4-imine, tetrahydro-3-methyl-N-nitro-5-[[2-(phenylthio)-5-thiazolyl]methyl]-

Product 1

HCID 107646n-(3-((2-Chlorothiazol-5-yl)methyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene)nitramide

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

183 g of 3-(2-phenylthio-thiazol-5-yl-methyl)-5-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine are introduced over a period of 5 minutes, with stirring, into a mixture of 300 g of hydrochloric acid (32%) and 150 g of chlorobenzene. 124 g of chlorine are introduced at 20° C. over a period of 4 hours. After 2 hours, excess chlorine is removed by the introduction of nitrogen, and the phases are then separated. The aqueous phase is adjusted to pH 5 with sodium hydroxide solution (30%) and then filtered, and the filtration residue is washed with water and dried in vacuo at 50° C. The title product is obtained in a purity of 97%.

Workup

  1. customexcess chlorine is removed by the introduction of nitrogen
  2. customthe phases are then separated
  3. filtrationfiltered
  4. washthe filtration residue is washed with water
  5. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-3aa1e863ace94704a4d3a61c4990e288
Source dataset
uspto-grants-2004_01
Patent number
US06677457B2

Reaction notes

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