Triethylamine → 2-[[O-[N-Methyl-N-(2-chloromethyl-2-propanesulfenyl)carbamoyl]oximino]]-1,4-dithiane

HRID 1980106Notes

Reaction equation

HRID 1980106 reaction equation
[CH3:1][N:2]([S:6][C:7]([CH2:10][Cl:11])([CH3:9])[CH3:8])[C:3](Cl)=[O:4].[N:12](=[C:14]1[CH2:19][S:18][CH2:17][CH2:16][S:15]1)[OH:13].C(N(CC)CC)C>O1CCOCC1.O>[CH3:1][N:2]([S:6][C:7]([CH2:10][Cl:11])([CH3:9])[CH3:8])[C:3]([O:13][N:12]=[C:14]1[CH2:19][S:18][CH2:17][CH2:16][S:15]1)=[O:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13363447N-methyl-N-(2-chloromethyl-2-propanesulfenyl)carbamoyl chlorideHCID 71364189N-1,4-Dithian-2-ylidenehydroxylamine

Product 1

HCID 542760462-[[O-[N-Methyl-N-(2-chloromethyl-2-propanesulfenyl)carbamoyl]oximino]]-1,4-dithiane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1.4 g of N-methyl-N-(2-chloromethyl-2-propanesulfenyl)carbamoyl chloride and 0.966 g of 2-oximino-1,4-dithiane in 50 ml of dioxane, was added dropwise with stirring 0.76 g of triethylamine. After allowing the reaction mixture to stand at ambient temperature for 16 hours it was diluted with water and extracted into ethylacetate. The organic extract was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The product was crystallized from isopropyl ether-methylene chloride solution. The weight of first crop was 1.0 g. m.p. 116°-117° C.

Workup

  1. extractionextracted into ethylacetate
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product was crystallized from isopropyl ether-methylene chloride solution

Sources & evidence

ORD record
ord-df4cfbb4f1a34cc88ea05f2ef03b9e6b
Source dataset
uspto-grants-1984_11
Patent number
US04485113

Reaction notes

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