Chloroacetyl chloride → 2-Chloro-1-(1-methyl-1H-pyrrol-2-yl)-ethanone
Reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.[Cl:7][CH2:8][C:9](Cl)=[O:10]>C1COCC1>[Cl:7][CH2:8][C:9]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=1)=[O:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 15 g (0.186 mole) N-methylpyrrole and 19.2 mL (0.186 mole) chloroacetyl chloride in 600 mL dry THF was heated under reflux overnight with a nitrogen stream bubbling through the reaction mixture. After cooling, the organics were washed with water, 1N NaOH, water, brine and dried (MgSO4). Evaporation of the solvent gave 31.2 g of a green solid: mp (decomp.) 280° C.; NMR 300 MHz (CDCl3) d 7.05 (d, 1H); 6.95 (s, 1H); 6.2 (m, 1H); 4.5 (s, 2H); 3.9 (s, 3H).
Workup
- temperatureunder reflux overnight with a nitrogen stream
- custombubbling through the reaction mixture
- temperatureAfter cooling
- washthe organics were washed with water, 1N NaOH, water, brine
- dry with materialdried (MgSO4)
- customEvaporation of the solvent
Sources & evidence
- ORD record
- ord-11a7197603db4a229920e1e1b2308b2d
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06191142B1
Reaction notes
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