Diethyl disulfide → HCID 21414079, compound

HRID 442290Notes

Reaction equation

HRID 442290 reaction equation
[CH2:1]([S:3][S:4][CH2:5][CH3:6])[CH3:2].S(Cl)([Cl:10])(=O)=O.[CH3:12][NH:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([Cl:24])[CH:18]=1)=[O:15]>N1C=CC=CC=1>[CH2:1]([S:3][Cl:10])[CH3:2].[CH3:12][N:13]([S:4][CH2:5][CH3:6])[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([Cl:24])[CH:18]=1)=[O:15]

Participants

6

Reactant 3

HCID 8077Diethyl disulfideHCID 24648Sulfuryl chlorideHCID 30967N-(3-chloro-4-methylphenyl)-N'-methylurea

Product 2

HCID 12275523ethanesulfenyl chlorideHCID 21414079HCID 21414079, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-40 °C

Procedure

Ethane sulfenyl chloride was prepared extemporaneously as in Example 9 from 68 g of diethyl disulfide and 67 g of sulfuryl chloride, cooled to -40° C. and a solution of 51.5 g of N-methyl-N'-(3-chloro-4-methylphenyl)-urea in 800 ml of pyridine were added thereto. The mixture was allowed to come to a temperature of -20° C. and was stirred for 11/2 hours at -20° C. The mixture was poured into a water-ice-hydrochloric acid mixture and was then extracted with methylene chloride. The organic phase was washed with water, dried and concentrated to dryness under reduced pressure and the residue was chromatographed over silica gel. The product was eluted with a 9-1 benzene-ethyl acetate mixture and the product was dissolved in ethyl ether. The ether solution was treated with activated carbon, filtered, and concentrated to dryness to obtain 19.5 g of N-methyl-N-ethylthio-N'-(3-chloro-4-methylphenyl)-urea melting at <50° C.

Workup

  1. customto come to a temperature of -20° C.
  2. extractionwas then extracted with methylene chloride
  3. washThe organic phase was washed with water
  4. customdried
  5. concentrationconcentrated to dryness under reduced pressure
  6. customthe residue was chromatographed over silica gel
  7. washThe product was eluted with a 9-1 benzene-ethyl acetate mixture
  8. dissolutionthe product was dissolved in ethyl ether
  9. additionThe ether solution was treated with activated carbon
  10. filtrationfiltered
  11. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b044dcf211f74f039884fbfdd6584efd
Source dataset
uspto-grants-1977_08
Patent number
US04045209

Reaction notes

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