Dimethylformamide → N-(1-propyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide

HRID 2290591Notes

Reaction equation

HRID 2290591 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.CN(C)C=O.C(Cl)(=O)OCC.[CH2:29]([N:32]1[CH2:36][CH2:35][CH2:34][CH:33]1[CH2:37][NH2:38])[CH2:30][CH3:31]>C(O)(C)C.C(N(CC)CC)C.CC(C)=O>[CH2:29]([N:32]1[CH2:36][CH2:35][CH2:34][CH:33]1[CH2:37][NH:38][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])[CH2:30][CH3:31]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 10928Ethyl chloroformateHCID 12829004(1-Propylpyrrolidin-2-YL)methanamineHCID 136908862-Methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid

Product 1

HCID 13420589N-(1-propyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3776IsopropanolSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 5 g of 2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid in a mixed solvent of 50 ml of dimethylformamide and 50 ml of acetone is added 6.5 ml of triethylamine 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 whole is stirred at room temperature for 40 minutes. Then, 3.3 of 1-propyl-2-aminomethylpyrrolidine is added and the reactant is stirred at room temperature for 40 minutes. After it is allowed to stand for 19 hours, excess triethylamine and acetone are distilled off and the resulting residue is slowly poured into 400 ml of water with stirring. Under ice-cooling, crystals are precipitated thoroughly and collected by suction filtration. The crystals are washed with water and dried. The filtrate, aqueous layer is further extracted with chloroform three times, and the extract chloroform layer is washed with aqueous sodium bicarbonate solution and water and dried. The chloroform is distilled off under reduced pressure and to the residue obtained is added isopropanol. Crystals are deposited and collected by suction filtration. Both the crude crystals are put together and recrystallized from isopropanol/methanol (1/1) to give crystals of N-(1-propyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide, m.p. 177°-180° C.

Workup

  1. temperatureUnder cooling at 15°-18° C
  2. stirringthe whole is stirred at room temperature for 40 minutes
  3. stirringthe reactant is stirred at room temperature for 40 minutes
  4. distillationexcess triethylamine and acetone are distilled off
  5. additionthe resulting residue is slowly poured into 400 ml of water
  6. stirringwith stirring
  7. temperatureUnder ice-cooling
  8. customcrystals are precipitated thoroughly
  9. filtrationcollected by suction filtration
  10. washThe crystals are washed with water
  11. customdried
  12. extractionThe filtrate, aqueous layer is further extracted with chloroform three times
  13. washthe extract chloroform layer is washed with aqueous sodium bicarbonate solution and water
  14. customdried
  15. distillationThe chloroform is distilled off under reduced pressure and to the residue
  16. customobtained
  17. filtrationcollected by suction filtration
  18. customrecrystallized from isopropanol/methanol (1/1)

Sources & evidence

ORD record
ord-d12b5194b1264d19bcb596b441dd7ab4
Source dataset
uspto-grants-1986_10
Patent number
US04617314

Reaction notes

Loading…