Hydrochloric Acid → HCID 21414089, compound

HRID 442289Notes

Reaction equation

HRID 442289 reaction equation
S(Cl)(Cl)(=O)=O.C(S[S:9][CH2:10][CH3:11])C.[CH3:12][NH:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([Cl:25])[CH:18]=1)=[O:15].Cl>C(Cl)Cl.N1C=CC=CC=1>[CH3:12][N:13]([S:9][CH2:10][CH3:11])[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([Cl:25])[CH:18]=1)=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8077Diethyl disulfideHCID 24648Sulfuryl chlorideHCID 30250Urea, N-(3-chloro-4-methoxyphenyl)-N'-methyl-

Product 1

HCID 21414089HCID 21414089, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

A mixture of 67 g of sulfuryl chloride and 100 ml of methylene chloride was slowly added at -40° C. to 68 g of diethyl disulfide in 600 ml of methylene chloride and after the temperature was slowly raised to -5° C., the mixture was stirred at -5° C. for 5 minutes. The mixture was then cooled to -40° C. and a solution of 56 g of N-methyl-N'-(3-chloro-4-methoxyphenyl)-urea in 800 ml of pyridine was added thereto. The mixture was stirred at -20° C. for 2 hours and was then added to a water-ice mixture. The pH of the mixture was adjusted to 5 by addition of an aqueous concentrated solution of hydrochloric acid and was extracted with methylene chloride. The combined organic extracts were washed with water until the wash water was neutral, then dried and distilled 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 crystallized from isopropyl ether to obtain 23.5 g of N-methyl-N-ethylthio-N'-(3-chloro-4-methoxyphenyl)-urea melting at 60° C.

Workup

  1. temperatureThe mixture was then cooled to -40° C.
  2. stirringThe mixture was stirred at -20° C. for 2 hours
  3. extractionwas extracted with methylene chloride
  4. washThe combined organic extracts were washed with water until the wash water
  5. customdried
  6. distillationdistilled to dryness under reduced pressure
  7. customThe residue was chromatographed over silica gel
  8. washeluted with a 7-3 benzene-ethyl acetate mixture
  9. customThe product was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-88a9673cf90e411692e1ae0e39a5ba05
Source dataset
uspto-grants-1977_08
Patent number
US04045209

Reaction notes

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