Methanol → Benzoic acid, 2-((2,6-dichloro-3-methylphenyl)amino)-, methyl ester
Reaction equation
[C:1](Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([Cl:25])=[C:12]([NH:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=2[C:22]([O-:24])=[O:23])[C:13]=1[Cl:14].[Na+].CN(C)C=O.CO>C(Cl)Cl>[Cl:14][C:13]1[C:8]([CH3:7])=[CH:9][CH:10]=[C:11]([Cl:25])[C:12]=1[NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=1[C:22]([O:24][CH3:1])=[O:23]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Oxalyl chloride (9.50 g, 74.8 mmol) in 20 ml of methylene chloride is added dropwise to a 0° C. suspension of meclomen (10.20 g, 34.4 mmol) and dimethylformamide (2.70 ml, 34.7 mmol) in 50 ml of methylene chloride. The clear yellow solution is stirred at 0° C. for 90 minutes then added by cannula to 110 ml of methanol at room temperature. The white suspension is stirred at room temperature overnight. The white solid is collected providing 7.52 g of product. The filtrate is concentrated and the residue partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over magnesium sulfate and concentrated, providing an additional 2.45 g of product (94% total), mp 130°-131° C.
Workup
- stirringThe white suspension is stirred at room temperature overnight
- customThe white solid is collected
Sources & evidence
- ORD record
- ord-88922598cb3543b5a30c2ca64c9ece3d
- Source dataset
- uspto-grants-1995_10
- Patent number
- US05462952
Reaction notes
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