Thionyl Chloride → 4-Amino-5-chloro-2,3-dihydro-7-benzofurancarbonyl chloride
Reaction equation
[NH2:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([C:11](O)=[O:12])=[CH:4][C:3]=1[Cl:14].S(Cl)([Cl:17])=O>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([C:11]([Cl:17])=[O:12])=[CH:4][C:3]=1[Cl:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4-amino-5-chloro-2,3-dihydro-7-benzofurancarboxylic acid (4.3 g) in thionyl chloride (100 ml) and CHCl3 (200 ml) was stirred and refluxed for 2 hours. The mixture was cooled and the solvent was evaporated. Toluene was added and evaporated again, yielding 4.8 g of 4-amino-5-chloro-2,3-dihydro-7-benzofurancarbonyl chloride (100% crude residue) (intermediate 7).
Workup
- temperaturerefluxed for 2 hours
- temperatureThe mixture was cooled
- customthe solvent was evaporated
- additionToluene was added
- customevaporated again
Sources & evidence
- ORD record
- ord-1043e9bb59bb4746884d7d3f2f8ad2eb
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05872131
Reaction notes
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