p-Toluenesulfonic acid → HCID 18979058, compound
Reaction equation
[F:1][C:2]1[C:3]([O:9][CH3:10])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:11]1(C)[CH:16]=CC(S(O)(=O)=O)=C[CH:12]=1.C(C=C)=O>ClC1C=CC=CC=1Cl>[F:1][C:2]1[C:3]([O:9][CH3:10])=[C:4]2[C:6]([CH:12]=[CH:11][CH:16]=[N:5]2)=[CH:7][CH:8]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 170 °C
Procedure
A solution of 3-fluoro 2-methoxyaniline (5.0 g) in 1,2-dichlorobenzene (50 ml) was heated to 170° C. and treated with p-toluenesulphonic acid (0.7 g). A solution of acrolein (4.0 g) in 1,2-dichlorobenzeue (20 ml) was added dropwise over 20 minutes. The reaction was stirred for 1 hour at 170° C. before being allowed to cool. The mixture was extracted with 2N hydrochloric acid (3×200 ml) and the combined extracts washed with dichloromethane (20 ml), basified with 25% aqueous sodium hydroxide, and extracted with ethyl acetate (3×200 ml). The combined extracts were dried over magnesium sulphate, filtered and the filtrate evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with 50% ethyl acetate in hexane to yield the desired product (2.6 g) as a clear oil.
Workup
- temperatureto cool
- extractionThe mixture was extracted with 2N hydrochloric acid (3×200 ml)
- washthe combined extracts washed with dichloromethane (20 ml)
- extractionextracted with ethyl acetate (3×200 ml)
- dry with materialThe combined extracts were dried over magnesium sulphate
- filtrationfiltered
- customthe filtrate evaporated in vacuo
- customThe residue was purified by column chromatography on silica gel eluting with 50% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-ea49f6b4fd8141778fc23f25c7c9f685
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05804588
Reaction notes
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