Pyridine → N-chlorothio-N-(3,4-dichlorophenyl)-N',N'-dimethyl urea

HRID 268106

Reaction equation

HRID 268106 reaction equation
[S:1]([Cl:3])Cl.[Cl:4][C:5]1[CH:6]=[C:7]([NH:12][C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH:8]=[CH:9][C:10]=1[Cl:11].N1C=CC=CC=1>C(Cl)Cl>[Cl:3][S:1][N:12]([C:7]1[CH:8]=[CH:9][C:10]([Cl:11])=[C:5]([Cl:4])[CH:6]=1)[C:13]([N:15]([CH3:16])[CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 3120DiuronHCID 25353Sulfur dichloride

Product 1

HCID 21314660N-chlorothio-N-(3,4-dichlorophenyl)-N',N'-dimethyl urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 5.7-g (0.055 mol) sample of sulfur dichloride was added dropwise to a mixture of 11.7 g (0.05 mol) of N-(3,4-dichlorophenyl)-N',N'-dimethyl urea and 4.7 g (0.06 mol) pyridine in 50 ml methylene chloride cooled in an ice bath. After the completion of the addition, the pyridine hydrochloride was filtered. Hexane was added to precipitate additional pyridine hydrochloride, which was removed by filtration. Evaporation of the resulting filtrate gave the product as a clear yellow oil. The NMR spectrum showed an N',N'-dimethyl singlet at 3.0 ppm (relative to tetramethylsilane). Elemental analysis showed:

Workup

  1. temperaturecooled in an ice bath
  2. additionAfter the completion of the addition
  3. filtrationthe pyridine hydrochloride was filtered
  4. additionHexane was added
  5. customto precipitate additional pyridine hydrochloride, which
  6. customwas removed by filtration
  7. customEvaporation of the resulting filtrate

Sources & evidence

ORD record
ord-d47b21a9c862486191a158b501967d1d
Source dataset
uspto-grants-1976_03
Patent number
US03946062

Linked notes

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