N,N-Dichlorourethan → 3,3,4,7-Tetrachloro-5-methoxy-1,3-dihydro-indol-2-one
Reaction equation
[Cl:1][C:2]1([Cl:15])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:12][CH3:13])[C:9]=2[Cl:11])[NH:4][C:3]1=[O:14].[Cl:16]N(Cl)C(OCC)=O>CC(O)=O>[Cl:15][C:2]1([Cl:1])[C:10]2[C:5](=[C:6]([Cl:16])[CH:7]=[C:8]([O:12][CH3:13])[C:9]=2[Cl:11])[NH:4][C:3]1=[O:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
11.54 g of 3,3,4-trichloro-5-methoxy-1 ,3-dihydro-indol-2-one (43.3 mmol) was suspended in glacial AcOH (200 mL). 3.343 g (21.7 mmol) of N,N-dichlorourethane was added and the mixture was stirred at 60° C. for 2 days. The reaction mixture was cooled to room temperature, the precipitate collected by filtration and dried on high vacuum. Re-crystallization from benzene (150 mL) yielded 6.135 g of product (containing 5% of the start. material as an impurity).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- filtrationthe precipitate collected by filtration
- customdried on high vacuum
Sources & evidence
- ORD record
- ord-0939d85c016f415081e9d900ef761e02
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07037909B2
Reaction notes
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