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

HRID 1954455Notes

Reaction equation

HRID 1954455 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)CCCCC1.[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 54229309HCID 54229309, compound

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

186 g of 3-(2-cyclohexylthio-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-7e05c050eba64f6fa29e69f77f4a2dd4
Source dataset
uspto-grants-2000_09
Patent number
US06121455

Reaction notes

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