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

HRID 2290586Notes

Reaction equation

HRID 2290586 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]2[CH:7]=[C:8]([S:15](=[O:18])(=[O:17])[NH2:16])[CH:9]=[C:10]([C:11]([O:13]C)=O)[C:4]=2[O:3]1.[CH2:19]([N:23]1[CH2:27][CH2:26][CH2:25][CH:24]1[CH2:28][NH2:29])[CH:20]([CH3:22])[CH3:21].O>C(O)COCCO>[CH2:19]([N:23]1[CH2:27][CH2:26][CH2:25][CH:24]1[CH2:28][NH:29][C:11]([C:10]1[C:4]2[O:3][CH:2]([CH3:1])[CH2:6][C:5]=2[CH:7]=[C:8]([S:15](=[O:18])(=[O:17])[NH2:16])[CH:9]=1)=[O:13])[CH:20]([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 13420574Methyl 2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylateHCID 14709035[1-(2-Methylpropyl)pyrrolidin-2-yl]methanamine

Product 1

HCID 13420581N-(1-isobutyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

A suspension of 5.2 g of methyl 2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylate and 4.5 g of 1-isobutyl-2-aminomethylpyrrolidine in 20 ml of diethylene glycol is heated at 130°-140° C. and stirred for 18-19 hours. The reaction solution is cooled to room temperature and poured into 150-200 ml of water while stirring. Under ice-cooling crystals are deposited thoroughly and collected by suction filtration. The crude crystals are washed with cold water, dissolved in chloroform and separated on a column of silica gel (developing solvent: methanol/chloroform=1/9). Crystals obtained are recrystallized from about 35 ml of methanol to give crystals of N-(1-isobutyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide, m.p. 182°-184° C.

Workup

  1. temperatureis heated at 130°-140° C.
  2. stirringwhile stirring
  3. temperatureUnder ice-cooling crystals
  4. filtrationcollected by suction filtration
  5. washThe crude crystals are washed with cold water
  6. dissolutiondissolved in chloroform
  7. customseparated on a column of silica gel (developing solvent: methanol/chloroform=1/9)
  8. customCrystals obtained
  9. customare recrystallized from about 35 ml of methanol

Sources & evidence

ORD record
ord-5afa806ec4f44f17b8a70f45c2ae6c65
Source dataset
uspto-grants-1986_10
Patent number
US04617314

Reaction notes

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