Allyl isocyanate → N-[2-(1,2-dichlorovinyloxy)phenylsulfonyl]-N'-allylurea
Reaction equation
[CH2:1]([N:4]=[C:5]=[O:6])[CH:2]=[CH2:3].[Cl:7][C:8]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18]([NH2:21])(=[O:20])=[O:19])=[CH:9][Cl:10].N12CCCN=C1CCCCC2>C(Cl)Cl>[Cl:7][C:8]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18]([NH:21][C:5]([NH:4][CH2:1][CH:2]=[CH2:3])=[O:6])(=[O:19])=[O:20])=[CH:9][Cl:10]Participants
5
Procedure
A solution of 3.3. g of allyl isocyanate in 10 ml of methylene chloride is added dropwise to a mixture of 10.7 g of 2-(1,2-dichlorovinyloxy)phenylsulfonamide and 6.1 g of 1,8-diazabicyclo[5.4.0]undec-7-ene in 100 ml of methylene chloride, with stirring. When the exothermic reaction has subsided, stirring of the reaction mixture is continued at 20° to 25° C. for a further hour and the solvent is then evaporated off. The residue is dissolved in 5% sodium carbonate solution. The solution is filtered and acidified with 10% hydrochloric acid, whereupon the product precipitates as crystals. After filtration and drying, 13.2 g of N-[2-(1,2-dichlorovinyloxy)phenylsulfonyl]-N'-allylurea are obtained. Melting point: 187°-188° C.
Workup
- customWhen the exothermic reaction
- stirringstirring of the reaction mixture
- waitis continued at 20° to 25° C. for a further hour
- customthe solvent is then evaporated off
- dissolutionThe residue is dissolved in 5% sodium carbonate solution
- filtrationThe solution is filtered
- customprecipitates as crystals
- filtrationAfter filtration
- customdrying
Sources & evidence
- ORD record
- ord-f69afe56f2fb4f319f4a34d0a1747d0d
- Source dataset
- uspto-grants-1985_12
- Patent number
- US04562210
Reaction notes
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