Ethyl chloroformate → N-(1-methyl-2-pyrrolidinyl-methyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide

HRID 2290592Notes

Reaction equation

HRID 2290592 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]2[CH:7]=[C:8]([S:14](=[O:17])(=[O:16])[NH2:15])[CH:9]=[C:10]([C:11]([OH:13])=O)[C:4]=2[O:3]1.C(Cl)(=O)OCC.[CH3:24][N:25]1[CH2:29][CH2:28][CH2:27][CH:26]1[CH2:30][NH2:31]>CN(C)C=O.CC(C)=O.C(N(CC)CC)C>[CH3:24][N:25]1[CH2:29][CH2:28][CH2:27][CH:26]1[CH2:30][NH:31][C:11]([C:10]1[C:4]2[O:3][CH:2]([CH3:1])[CH2:6][C:5]=2[CH:7]=[C:8]([S:14](=[O:17])(=[O:16])[NH2:15])[CH:9]=1)=[O:13]

Participants

7

Reactant 3

HCID 10928Ethyl chloroformateHCID 1173001-Methylpyrrolidine-2-methylamineHCID 136908862-Methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid

Product 1

HCID 13420590N-(1-methyl-2-pyrrolidinyl-methyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

2-Methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid, 5.0 g, is dissolved in a mixed solvent of 50 ml of dimethylformamide and 50 ml of acetone, 6.5 ml of triethylamine is added and the solution is stirred. Under cooling at 15°-18° C., 2.2 g of ethyl chlorocarbonate is added dropwise for 10 minutes, and the solution is stirred at room temperature for one hour. Thereafter, 2.7 g of 1-methyl-2-aminomethylpyrrolidine is added and the whole is stirred at room temperature for 3 hours and allowed to stand for 15 hours. Excess triethylamine and acetone are distilled off under reduced pressure and the resulting residue is poured into 300-400 ml of water. The aqueous layer is extracted via with chloroform three times and the extract layer is washed with aqueous sodium bicarbonate solution, water and sodium chloride saturated water in this sequence. After drying, the chloroform is distilled off under reduced pressure and the residue obtained is recrystallized from ethyl acetate to give crystals of N-(1-methyl-2-pyrrolidinyl-methyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide, m.p. 187°-189° C.

Workup

  1. additionis added
  2. temperatureUnder cooling at 15°-18° C.
  3. stirringthe solution is stirred at room temperature for one hour
  4. stirringthe whole is stirred at room temperature for 3 hours
  5. distillationExcess triethylamine and acetone are distilled off under reduced pressure
  6. additionthe resulting residue is poured into 300-400 ml of water
  7. extractionThe aqueous layer is extracted via with chloroform three times
  8. washthe extract layer is washed with aqueous sodium bicarbonate solution, water and sodium chloride saturated water in this sequence
  9. customAfter drying
  10. distillationthe chloroform is distilled off under reduced pressure
  11. customthe residue obtained
  12. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4baf03cceb5b4e99b30c099688c8ba7f
Source dataset
uspto-grants-1986_10
Patent number
US04617314

Reaction notes

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