Chloroacetyl chloride → 2-Chloro-1-(1-methyl-1H-pyrrol-2-yl)-ethanone

HRID 1729181Notes

Reaction equation

HRID 1729181 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

HCID 6577Chloroacetyl chlorideHCID 73041-Methylpyrrole

Product 1

HCID 25124042-Chloro-1-(1-methyl-1H-pyrrol-2-yl)-ethanoneYield 106.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. temperatureunder reflux overnight with a nitrogen stream
  2. custombubbling through the reaction mixture
  3. temperatureAfter cooling
  4. washthe organics were washed with water, 1N NaOH, water, brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c5b2aef87b6b4b58b512059d3ec68287
Source dataset
uspto-grants-1994_07
Patent number
US05332736

Reaction notes

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