Water → HCID 21391467, compound

HRID 1415092Notes

Reaction equation

HRID 1415092 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]Cl)=[CH:4][CH:3]=1.[Cl:10][C:11]1[N:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([N:24](C)[C:25]([NH2:27])=[O:26])=[CH:20][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.N1C=CC=C[CH:30]=1.O>CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][N:27]([CH3:30])[C:25]([NH:24][C:21]2[CH:20]=[CH:19][C:18]([O:17][C:15]3[CH:14]=[CH:13][CH:12]=[C:11]([Cl:10])[N:16]=3)=[CH:23][CH:22]=2)=[O:26])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 110844654-ChlorobenzenesulfenylchlorideHCID 86732873HCID 86732873, compound

Product 1

HCID 21391467HCID 21391467, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
30 °C

Procedure

4-Chlorobenzenesulfenyl chloride (8.68 grams; 0.0496 mole) was added over a period of about 3 minutes to a solution of N'-(4-((6-chloro-2-pyridinyl)oxy)phenyl-N-methylurea (8.3 grams; 0.03 mole) in 50 ml. of dry pyridine. The resulting reaction mixture was stirred at a temperature of about 30° C. for a period of about 1 and one-half hours and then poured into 250 ml. of cold water. The resulting sticky product precipitate was dissolved in hot hexane, reprecipitated therefrom upon standing and the light-yellow, slightly sticky product obtained triturated with a small amount of cold acetonitrile. Filtration of the mixture gave the desired N-((4-chlorophenyl)thio)-N'-(4-((6-chloro-2-pyridinyl)oxy)phenyl)-N-methylurea compound as a white crystalline solid melting at 106°-109° C. The product was found to have carbon, hydrogen, nitrogen, chlorine and sulfur contents of 54.2, 3.5, 9.86, 17.0 and 7.46 percent, respectively, as compared with contents of 54.3, 3.6, 10.0, 16.87 and 7.6 percent, respectively, as calculated for the named structure.

Workup

  1. customThe resulting reaction mixture
  2. additionpoured into 250 ml
  3. customreprecipitated
  4. customthe light-yellow, slightly sticky product obtained
  5. customtriturated with a small amount of cold acetonitrile
  6. filtrationFiltration of the mixture

Sources & evidence

ORD record
ord-fc932979d4e64ad5baf37464c8cd0f27
Source dataset
uspto-grants-1977_01
Patent number
US04003734

Reaction notes

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