Dichloromethane → N-methyl-N-(2-chlorocyclooctylthio)-N'-(3,4-dichlorophenyl) urea

HRID 268107

Reaction equation

HRID 268107 reaction equation
[CH2:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[S:10][N:11]([CH3:23])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)=[O:13].C(Cl)[Cl:25]>>[CH3:23][N:11]([S:10][CH:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[Cl:25])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)=[O:13]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 9266CyclooctaneHCID 21314661N-chlorothio-N-methyl-N'-(3,4-dichlorophenyl) urea

Product 1

HCID 54070333N-methyl-N-(2-chlorocyclooctylthio)-N'-(3,4-dichlorophenyl) urea

Procedure

An 11.0-g (0.1 mol) sample of cyclooctane was added dropwise at 0°C. to a solution of 0.1 mol N-chlorothio-N-methyl-N'-(3,4-dichlorophenyl) urea, prepared by a procedure similar to that of Example 3, in methylene dichloride. After the addition was completed, the reaction mixture was washed successively with water, aqueous sodium bicarbonate solution and water, dried over magnesium sulfate and evaporated to give a solid residue. The solid was recrystallized from isopropyl alcohol and washed with hexane to give 15 g of product, m.p. 90°-91°C. Elemental analysis for C16H21Cl3N2OS showed: %S, calc. 8.1, found 8.2; %Cl, calc. 26.9, found 27.4.

Workup

  1. customprepared by a procedure similar to that of Example 3
  2. additionAfter the addition
  3. washthe reaction mixture was washed successively with water, aqueous sodium bicarbonate solution and water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give a solid residue
  7. customThe solid was recrystallized from isopropyl alcohol
  8. washwashed with hexane

Sources & evidence

ORD record
ord-a2736e8c9947448eb3dc6696adab7f93
Source dataset
uspto-grants-1976_03
Patent number
US03946062

Linked notes

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