Sodium Carbonate → HCID 58305608, compound

HRID 1188281Notes

Reaction equation

HRID 1188281 reaction equation
O=P(Cl)(Cl)Cl.[CH3:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1)[C:10]([NH2:12])=O.[C:21]([O-])([O-])=[O:22].[Na+].[Na+]>CN(C=O)C>[CH:21]([C:17]1[N:16]([C:15]2[CH:14]=[CH:13][C:9]([C:10]#[N:12])=[CH:8][C:7]=2[CH3:6])[CH:20]=[CH:19][CH:18]=1)=[O:22]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 58305652HCID 58305652, compound

Product 1

HCID 58305608HCID 58305608, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

POCl3 (65 g, 427 mmol) was added to DMF (34 mL) at 0° C. for 30 min. After addition, the mixture was stirred at room temperature for 1.5 h, and then cooled to 0° C. A solution of 3-methyl-4-(1H-pyrrol-1-yl)benzamide (6A) (42.7 g, 213.5 mmol) in DMF (150 mL) was added at 0° C. and the resultant mixture was stirred at room temperature for 20 min, and then heated to 80° C. for 1 h. The solution was cooled to room temperature and then sat. Na2CO3 was added at 0° C. until pH=8. The mixture was extracted with ethyl acetate three times. The combined organic layers were washed with sat. NaHCO3 and brine, dried over Na2SO4, concentrated and purified by silica gel column chromatography (PE:EA=10:1) to afford 4-(2-formyl-1H-pyrrol-1-yl)-3-methylbenzonitrile as a yellow solid (30.5 g, yield 68%).

Workup

  1. additionAfter addition
  2. temperaturecooled to 0° C
  3. temperatureheated to 80° C. for 1 h
  4. temperatureThe solution was cooled to room temperature
  5. extractionThe mixture was extracted with ethyl acetate three times
  6. washThe combined organic layers were washed with sat. NaHCO3 and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography (PE:EA=10:1)

Sources & evidence

ORD record
ord-0c17ac92768e44f8abdf7e2b5df1146f
Source dataset
uspto-grants-2014_03
Patent number
US08673961B2

Reaction notes

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