Hydrochloric Acid → HCID 67639316, compound
Reaction equation
[C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].C[N:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][C:23]([O:25][CH3:26])=[O:24].Cl.[CH2:28](Cl)Cl>>[C:1]([C:21]1[NH:17][C:18]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[C:19]([CH3:28])[CH:20]=1)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1Participants
Procedure
A solution of 17.0 g. (0.1 mole) of ρ-anisoyl chloride and 13.3 g. (0.1 mole) of aluminum chloride in 200 ml. of methylene chloride is added over 5 minutes to a solution of methyl 1-methylpyrrole-2-acetate in 100 ml. of methylene chloride at ice bath temperature. The mixture is stirred for 25 minutes and poured into ice acidified with dilute hydrochloric acid. The organic layer is separated, and the aqueous layer is washed with methylene chloride. The combined organic solutions are washed successively with dimethylaminopropylamine solution, dilute hydrochloric acid and brine, and then dried over anhydrous magnesium sulfate. The solvent is evaporated in vacuo to give a dark oily residue which is crystallized from 40 ml. of cold methanol, and recrystallized from methanol to give white crystalline methyl 5-(ρ-anisoyl)-methylpyrrole-2-acetate, M.P. 104°-105° C.
Workup
- additionpoured into ice
- customThe organic layer is separated
- washthe aqueous layer is washed with methylene chloride
- washThe combined organic solutions are washed successively with dimethylaminopropylamine solution, dilute hydrochloric acid and brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent is evaporated in vacuo
- customto give a dark oily residue which
- customis crystallized from 40 ml
- customof cold methanol, and recrystallized from methanol
Sources & evidence
- ORD record
- ord-0a697ad121654f8fb7ce4b15225fc5b4
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05721347
Reaction notes
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