Benzenamine, 4-chloro-2-methoxy- → N-(4-chloro-2-methoxyphenyl)-2,2-dimethylpropanamide
Reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[CH:3]=1.C(N(CC)CC)C.[CH3:18][C:19]([CH3:24])([CH3:23])[C:20](Cl)=[O:21]>O1CCCC1.C(Cl)Cl>[CH3:18][C:19]([CH3:24])([CH3:23])[C:20]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][C:4]=1[O:9][CH3:10])=[O:21]Participants
Procedure
In to a stirred solution containing 10.0 grams (0.06 mole) of 4-chloro-2-methoxyaniline and 6.42 grams (0.06 mole) of triethylamine in 200 milliliters of tetrahydrofuran was added 7.65 grams (0.06 mole) of trimethylacetyl chloride in a small amount of tetrahydrofuran solvent. The resulting mixture was stirred for two hours at room temperature. Triethylamine hydrochloride precipitated and was filtered off and the filtrate vacuum stripped to give a dark liquid which was taken up in methylene chloride. This solution was washed with 2N HCl (2×100 milliliters), then with water (1×100 milliliters), dried over magnesium sulfate and solvent evaporated to give a crude product which was crystallized from hexane to give 6.82 grams (0.03 mole) of 2,2-dimethyl-N-(4-chloro-2-methoxyphenyl)propanamide as a first and second crop. NMR analysis of the product indicated the following:
Workup
- customTriethylamine hydrochloride precipitated
- filtrationwas filtered off
- customto give a dark liquid which
- washThis solution was washed with 2N HCl (2×100 milliliters)
- dry with materialwith water (1×100 milliliters), dried over magnesium sulfate and solvent
- customevaporated
- customto give a crude product which
- customwas crystallized from hexane
Sources & evidence
- ORD record
- ord-d5a46eca605b4d76bb6ff38c5427a2de
- Source dataset
- uspto-grants-1992_06
- Patent number
- US05123951
Reaction notes
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