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

HRID 322806Notes

Reaction equation

HRID 322806 reaction equation
C(S[C:9]1[S:10][C:11]([CH2:14][N:15]2[C:20](=[N:21][N+:22]([O-:24])=[O:23])[N:19]([CH3:25])[CH2:18][O:17][CH2:16]2)=[CH:12][N:13]=1)C1C=CC=CC=1.[Cl:26]CCl.[O-]Cl.[Na+]>Cl>[Cl:26][C:9]1[S:10][C:11]([CH2:14][N:15]2[C:20](=[N:21][N+:22]([O-:24])=[O:23])[N:19]([CH3:25])[CH2:18][O:17][CH2:16]2)=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 23665760Sodium HypochloriteHCID 541069703-(2-Benzylthiothiazol-5-ylmethyl)-5-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine

Product 1

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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2 g of 3-(2-benzylthiothiazol-5-ylmethyl)-5-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine are dissolved in a mixture of 10 ml of 4N aqueous hydrochloric acid, 20 g of ice and 30 ml of dichloromethane, and 30 g of Javelle water are added dropwise with stirring to the solution. After stirring for a further 30 minutes, the organic phase is separated off, the aqueous phase is extracted repeatedly with a little dichloromethane, and the combined organic phases are subsequently dried with sodium sulphate and evaporated under reduced pressure. The oily residue is dissolved in tetrahydrofuran and precipitated with hexane, whereby the product deposits on the walls of the vessel as a sticky material. The solvent is decanted, the residue is redissolved in tetrahydrofuran, and the solution is slowly concentrated, yielding 0.84 g of the title compound in the form of a semi-crystalline resin. A sample of this resin is purified by chromatography [silica gel; dichloromethane/methanol (95:5)], yielding crystals melting at 132 to 135°.

Workup

  1. additionare added dropwise
  2. stirringAfter stirring for a further 30 minutes
  3. customthe organic phase is separated off
  4. extractionthe aqueous phase is extracted repeatedly with a little dichloromethane
  5. dry with materialthe combined organic phases are subsequently dried with sodium sulphate
  6. customevaporated under reduced pressure
  7. dissolutionThe oily residue is dissolved in tetrahydrofuran
  8. customprecipitated with hexane, whereby the product deposits on the walls of the vessel as a sticky material
  9. customThe solvent is decanted
  10. dissolutionthe residue is redissolved in tetrahydrofuran
  11. concentrationthe solution is slowly concentrated

Sources & evidence

ORD record
ord-898733b7195842f7a9e21f946a333843
Source dataset
uspto-grants-2001_04
Patent number
US06211381B1

Reaction notes

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