4-Chlorobenzoyl chloride → 5-(p-Chlorobenzoyl)-2-methoxycarbonyl-4-methylthio-1-methylpyrrole

HRID 1388926Notes

Reaction equation

HRID 1388926 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:15][O:16][C:17]([C:19]1[N:20]([CH3:26])[CH:21]=[C:22]([S:24][CH3:25])[CH:23]=1)=[O:18]>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:21]2[N:20]([CH3:26])[C:19]([C:17]([O:16][CH3:15])=[O:18])=[CH:23][C:22]=2[S:24][CH3:25])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 13345725Methyl 1-methyl-4-(methylsulfanyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 204690975-(p-Chlorobenzoyl)-2-methoxycarbonyl-4-methylthio-1-methylpyrroleYield 30.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

p-Chlorobenzoyl chloride (2.75 ml, 20 mmol), dissolved 20 ml of methylene chloride and 2.6 g (20 mmol) of aluminum chloride are mixed well at room temperature. After about 5 minutes 1.87 g (10 mmole) of 2-methoxycarbonyl-4-methylthio-1-methylpyrrole is added dropwise. The reaction mixture turns immediately into a dark red colored solution. The reaction is stirred for one hour before it is diluted with 75 ml of methylene chloride and extracted with water. The methylene chloride layer is separated, washed sucessively with 25 ml sodium bicarbonate solution and 50 ml of saturated brine, dried over anhydrous sodium sulfate and concentrated to an oil. The oil is crystallized from ethanol to give 1.0 g of 5-(p-chlorobenzoyl)-2-methoxycarbonyl-4-methylthio-1-methylpyrrole.

Workup

  1. additionare mixed well at room temperature
  2. extractionextracted with water
  3. customThe methylene chloride layer is separated
  4. washwashed sucessively with 25 ml sodium bicarbonate solution and 50 ml of saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to an oil
  7. customThe oil is crystallized from ethanol

Sources & evidence

ORD record
ord-233a0f9f588c4c8abfc04824658be01a
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Reaction notes

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