Hydrochloric Acid → HCID 21414093, compound

HRID 442291Notes

Reaction equation

HRID 442291 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]([Br:23])=[CH:19][CH:18]=1)=[O:15].Cl>N1C=CC=CC=1.O>[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]([Br:23])=[CH:19][CH:18]=1)=[O:15]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8077Diethyl disulfideHCID 24648Sulfuryl chlorideHCID 152311N-(4-Bromophenyl)-N'-methylcarbamimidato(3-)

Product 2

HCID 12275523ethanesulfenyl chlorideHCID 21414093HCID 21414093, compoundYield 43.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
-40 °C

Procedure

Ethane sulfenyl chloride was prepared as in Example 9 from 68 g of diethyldisulfide and 67 g of sulfuryl chloride, cooled to -40° C. and a solution of 60 g of N-methyl-N'-(4-bromophenyl)-urea in 800 ml of pyridine was added thereto. After stirring the reaction mixture for 30 minutes at -40° C., the temperature was allowed to rise to -20° C. and the mixture was stirred for 11/2 hours at this temperature. The mixture was poured into a mixture of water, ice and hydrochloric acid and was extracted with methylene chloride. The organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and eluted with a 7-3 benzene-ethyl acetate mixture. The product was dissolved in ethyl ether and the solution was treated with activated carbon, filtered and concentrated to dryness under reduced pressure. The residue was added to petroleum ether (b.p. = 65°-75° C.) and the precipitate formed was recovered by vacuum filtration to obtain 33 g of N-methyl-N-ethylthio-N'-(4-bromophenyl)-urea melting at <50° C.

Workup

  1. customto rise to -20° C.
  2. stirringthe mixture was stirred for 11/2 hours at this temperature
  3. extractionwas extracted with methylene chloride
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was chromatographed over silica gel
  8. washeluted with a 7-3 benzene-ethyl acetate mixture
  9. dissolutionThe product was dissolved in ethyl ether
  10. additionthe solution was treated with activated carbon
  11. filtrationfiltered
  12. concentrationconcentrated to dryness under reduced pressure
  13. additionThe residue was added to petroleum ether (b.p. = 65°-75° C.)
  14. customthe precipitate formed
  15. filtrationwas recovered by vacuum filtration

Sources & evidence

ORD record
ord-ab79decd3fe44868804ace9c94a6281c
Source dataset
uspto-grants-1977_08
Patent number
US04045209

Reaction notes

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