Sodium Carbonate → HCID 58305652, compound

HRID 1188280Notes

Reaction equation

HRID 1188280 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)O1.[NH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][C:12]=1[CH3:20].C([O-])([O-])=O.[Na+].[Na+]>CC(O)=O>[CH3:20][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:11]=1[N:10]1[CH:3]=[CH:7][CH:6]=[CH:5]1)[C:15]([NH2:17])=[O:16]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 790982,5-DimethoxytetrahydrofuranHCID 121180574-amino-3-methylbenzamide

Product 1

HCID 58305652HCID 58305652, compoundYield 671.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

The 2,5-dimethoxy-tetrahydrofuran (106 g, 80 mmol) was added to the solution of 4-amino-3-methylbenzamide (100 g, 66.7 mmol) in AcOH (300 mL). The mixture was stirred at 80° C. for about 1.5 h and then cooled to room temperature. The solution of Na2CO3 was added dropwise at 0° C. and extracted with ethyl acetate for three times. The combined organic layers were washed with brine, dried over Na2SO4, concentrated and washed with petroleum ether. The resultant solid was filtrated and dried to afford 3-methyl-4-(1H-pyrrol-1-yl)benzamide as a pale solid (89.7 g, yield 67%).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate for three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. washwashed with petroleum ether
  7. filtrationThe resultant solid was filtrated
  8. customdried

Sources & evidence

ORD record
ord-92616baeae694763b69dc389cc367170
Source dataset
uspto-grants-2014_03
Patent number
US08673961B2

Reaction notes

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