Chloroacetyl chloride → 4-(Chloroacetyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde

HRID 1828898Notes

Reaction equation

HRID 1828898 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[CH:10]=[C:9]([CH3:11])[NH:8][C:7]=1[CH:12]=[O:13].[Cl:14][CH2:15][C:16](Cl)=[O:17]>ClCCCl>[Cl:14][CH2:15][C:16]([C:10]1[C:6]([CH3:5])=[C:7]([CH:12]=[O:13])[NH:8][C:9]=1[CH3:11])=[O:17]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 2704653,5-Dimethyl-1H-pyrrole-2-carbaldehydeHCID 6451240Aluminum(III) Chloride

Product 1

HCID 220598554-(Chloroacetyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehydeYield 57%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Anhydrous aluminum chloride (42 g, 315 mmol) was added portionwise over 30 min to a room temperature solution of 3,5-dimethylpyrrol-2-carboxaldehyde (5 g, 40 mmol) in 1,2-dichloroethane (50 ml) under nitrogen. After stirring for 15 min, chloroacetyl chloride (17 g, 150 mmol) was added dropwise over 1 h. After addition was complete, the mixture was stirred at room temperature for 16 h. The mixture was poured onto crushed ice and the organic layer separated, dried over anhydrous sodium sulfate, and the solvent removed under reduced pressure. Yield 57%, m.p. 205–09° C. (toluene).

Workup

  1. additionAfter addition
  2. stirringthe mixture was stirred at room temperature for 16 h
  3. additionThe mixture was poured
  4. customonto crushed ice
  5. customthe organic layer separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e226a92232d04cdc97ffba1e1b7b32aa
Source dataset
uspto-grants-2006_06
Patent number
US07060822B1

Reaction notes

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