Hydrochloric Acid → N-(2-chloroethylthio)-N-methyl-N'-(3,4-dichlorophenyl)-urea

HRID 441902Notes

Reaction equation

HRID 441902 reaction equation
S(Cl)(=O)(=O)O.[CH2:6]1[S:8][CH2:7]1.[CH3:9][NH:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)=[O:12].[ClH:22]>N1C=CC=CC=1.C(Cl)Cl.O>[Cl:22][CH2:7][CH2:6][S:8][N:10]([CH3:9])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)=[O:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 9865ThiiraneHCID 19113MonomethyldiuronHCID 24638Chlorosulfonic acid

Product 1

HCID 21415679N-(2-chloroethylthio)-N-methyl-N'-(3,4-dichlorophenyl)-urea

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

27 g of chlorosulfuric acid were slowly added at 0° C to a mixture of 12 g of ethylene sulfide and 200 ml of methylene chloride and the mixture was stirred at 0° C for 10 minutes and was then cooled to -20° C. A mixture of 32.6 g of N-methyl-N'-(3,4-dichlorophenyl)-urea in 210 ml of pyridine was added to the reaction mixture after which the temperature returned to 0° C. The mixture was stirred at 0° C for 10 minutes and was then poured into a mixture of ice, water, hydrochloric acid and methylene chloride. The mixture was stirred for 30 minutes and the decanted organic phase was washed, dried, filtered and concentrated to dryness under reduced pressure. The residue was chromatographed over silica gel and the product was eluted witn 9-1 benzene-ethyl acetate mixture and was crystallized from isopropyl ether to obtain 10 g of N-(2-chloroethylthio)-N-methyl-N'-(3,4-dichlorophenyl)-urea melting at 62° C.

Workup

  1. temperaturewas then cooled to -20° C
  2. additionwas added to the reaction mixture after which the temperature
  3. customreturned to 0° C
  4. stirringThe mixture was stirred at 0° C for 10 minutes
  5. stirringThe mixture was stirred for 30 minutes
  6. washthe decanted organic phase was washed
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure
  10. customThe residue was chromatographed over silica gel
  11. washthe product was eluted witn 9-1 benzene-ethyl acetate mixture
  12. customwas crystallized from isopropyl ether

Sources & evidence

ORD record
ord-0f9f668dae6046e9932609fff27afe29
Source dataset
uspto-grants-1977_08
Patent number
US04043796

Reaction notes

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