Potassium Hydroxide → 2-[O-(N-Dimethylaminosulfenyl-N-methylcarbamoyl)oximino]-3,3-dimethyltetrahydro-1,4-thiazin-5-one

HRID 1834888Notes

Reaction equation

HRID 1834888 reaction equation
[N:1](=[C:3]1[C:8]([CH3:10])([CH3:9])[NH:7][C:6](=[O:11])[CH2:5][S:4]1)[OH:2].O1CCOCC1.[OH-].[K+].[CH3:20][N:21]([S:25][N:26]([CH3:28])[CH3:27])[C:22](F)=[O:23]>C1CC2OCCOCCOC3C(OCCOCCOC2CC1)CCCC3.O>[CH3:27][N:26]([CH3:28])[S:25][N:21]([CH3:20])[C:22]([O:2][N:1]=[C:3]1[C:8]([CH3:9])([CH3:10])[NH:7][C:6](=[O:11])[CH2:5][S:4]1)=[O:23]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 12799216N-methyl-N-(dimethylaminosulfenyl)carbamoyl fluorideHCID 713869496-(Hydroxyimino)-5,5-dimethylthiomorpholin-3-one

Product 1

HCID 542539312-[O-(N-Dimethylaminosulfenyl-N-methylcarbamoyl)oximino]-3,3-dimethyltetrahydro-1,4-thiazin-5-oneYield 68.6%

Reagents, catalysts & solvents 2

HCID 85955Dicyclohexano-18-crown-6CatalystHCID 962WaterSolvent

Procedure

A mixture of 5.8 g of 2-oximino-3,3-dimethyltetrahydro-1,4-thiazin-5-one, 200 ml dioxane, 2.1 g powdered potassium hydroxide and 0.1 g dicyclohexyl-18-crown-6, was charged to a stirred flask and 5.3 g of N-methyl-N-(dimethylaminosulfenyl)carbamoyl fluoride was added at 30° C over a 1-minute period. The reaction mixture was stirred overnight at room temperature and then added to cold water and stirred for 5 minutes. The resulting mixture was extracted with methylene chloride. The methylene chloride layer was washed thoroughly with water and then dried with magnesium sulfate. The methylene chloride was stripped from the product under reduced pressure and the crystalline residue was recrystallized from ethylene acetate to provide 7.0 g of 2-[O-(N-Dimethylaminosulfenyl-N-methylcarbamoyl)oximino]-3,3-dimethyltetrahydro-1,4-thiazin-5-one, m.p. 165°-167° C. An nmr spectrum supported the proposed structure.

Workup

  1. additionwas charged to a stirred flask
  2. stirringstirred for 5 minutes
  3. extractionThe resulting mixture was extracted with methylene chloride
  4. washThe methylene chloride layer was washed thoroughly with water
  5. dry with materialdried with magnesium sulfate
  6. customthe crystalline residue was recrystallized from ethylene acetate

Sources & evidence

ORD record
ord-ac3c7f305bd2427b899bfa08c8539b4d
Source dataset
uspto-grants-1978_01
Patent number
US04071627

Reaction notes

Loading…