Dimethyl Sulfoxide → N-methyl-N-(2-thiapropyl)-N'-(3,4-dichlorophenyl)-urea

HRID 442287Notes

Reaction equation

HRID 442287 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].C[S](Cl)C.[CH3:24][S:25]([CH3:27])=O>O>[CH3:1][N:2]([CH2:24][S:25][CH3:27])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)=[O:4]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 19113MonomethyldiuronHCID 85662010CID 85662010

Product 1

HCID 21414071N-methyl-N-(2-thiapropyl)-N'-(3,4-dichlorophenyl)-urea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

11 g of N-methyl-N'-(3,4-dichlorophenyl)-urea, 60 g of potassium carbonate and 50 ml of dimethylsulfur chloride were added at 10° C. to 150 ml of dimethylsulfoxide and the mixture was allowed to stand until exothermic generation of heat ceased. The reaction mixture was added to water and was extracted with ether. The ether solution was washed with water, dried and concentrated to dryness by distillation under reduced pressure. The residue was crystallized from isopropyl ether and then ethyl acetate to obtain 7.7 g of N-methyl-N-(2-thiapropyl)-N'-(3,4-dichlorophenyl)-urea melting at 103° C.

Workup

  1. temperatureof heat
  2. extractionwas extracted with ether
  3. washThe ether solution was washed with water
  4. customdried
  5. concentrationconcentrated to dryness by distillation under reduced pressure
  6. customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-60e49ab061c7448c8ceffccf92a7a3f9
Source dataset
uspto-grants-1977_08
Patent number
US04045209

Reaction notes

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