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

HRID 322808Notes

Reaction equation

HRID 322808 reaction equation
[ClH:1].C1(S[C:9]2[S:10][C:11]([CH2:14][N:15]3[C:20](=[N:21][N+:22]([O-:24])=[O:23])[N:19]([CH3:25])[CH2:18][O:17][CH2:16]3)=[CH:12][N:13]=2)CCCCC1.ClCl>ClC1C=CC=CC=1>[Cl:1][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 313Hydrochloric AcidHCID 24526ChlorineHCID 54229309HCID 54229309, compound

Product 1

HCID 107646n-(3-((2-Chlorothiazol-5-yl)methyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene)nitramideYield 92.4%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a mixture of 300 g of aqueous hydrochloric acid (32%) and 150 g of chlorobenzene are added with stirring 186 g of 3-(2-cyclohexylthiothiazol-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 135 g of the title compound (purity: 97%) melting at 132 to 135°.

Workup

  1. additionare added
  2. customthe excess of chlorine is removed by introduction of nitrogen
  3. additionthe aqueous phase (containing the title compound in hydrochloride form)
  4. customis separated off
  5. filtrationThe crystalline precipitate is filtered off
  6. washwashed with water
  7. customdried at 50° in vacuo

Sources & evidence

ORD record
ord-ce75d2956fda45538704b93316735bb8
Source dataset
uspto-grants-2001_04
Patent number
US06211381B1

Reaction notes

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