Triethylamine → 2-[O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oximino]-3,3-dimethyltetrahydro-1,4-thiazin-5-one

HRID 1834886Notes

Reaction equation

HRID 1834886 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.[CH3:18][N:19]([S:23][C:24]([Cl:27])([Cl:26])[Cl:25])[C:20](F)=[O:21].C(N(CC)CC)C>O>[CH3:18][N:19]([S:23][C:24]([Cl:27])([Cl:26])[Cl:25])[C:20]([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:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 12836648Methyl[(trichloromethyl)sulfanyl]carbamyl fluorideHCID 713869496-(Hydroxyimino)-5,5-dimethylthiomorpholin-3-one

Product 1

HCID 536645372-[O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oximino]-3,3-dimethyltetrahydro-1,4-thiazin-5-oneYield 39.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.5 g of 2-oximino-3,3-dimethyltetrahydro-1,4-thiazin-5-one, dioxane and N-methyl-N-(trichloromethylthio)carbamoyl fluoride (4.5 g) was charged to a stirred flask and 2.1 g of triethylamine was added dropwise at 30° C, over a 2-minute period. The reaction mixture was stirred overnight at room temperature. The reaction mixture was then added to cold water and stirred for 10 minutes. The crystalline solid was filtered, washed thoroughly with water and dried overnight. After drying the crude product was recrystallized from isopropanol to yield 3 g of 2-[O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oximino]-3,3-dimethyltetrahydro-1,4-thiazin-5-one, m.p. 189°-190° C. The nmr spectrum of this material was consistent with its proposed structure.

Workup

  1. additionwas charged to a stirred flask
  2. stirringstirred for 10 minutes
  3. filtrationThe crystalline solid was filtered
  4. washwashed thoroughly with water
  5. customdried overnight
  6. dry with materialAfter drying the crude product
  7. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-12f0a5c16b664af0813a959118fd5d93
Source dataset
uspto-grants-1978_01
Patent number
US04071627

Reaction notes

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