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

HRID 841055Notes

Reaction equation

HRID 841055 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-phenylthiothiazol-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-66eb80b7e2ca4557b4e04a79b0cd5cb6
Source dataset
uspto-grants-2002_04
Patent number
US06369233B1

Reaction notes

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