Water → N-[(1-butylpyrrolidin-2-yl)methyl]-2-methyl-5-sulfamoyl-2,3-dihydro-1-benzofuran-7-carboxamide

HRID 2290587Notes

Reaction equation

HRID 2290587 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])[CH2:20][CH2:21][CH3:22].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])[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 12829006(1-Butylpyrrolidin-2-YL)methanamineHCID 13420574Methyl 2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylate

Product 1

HCID 130282N-[(1-butylpyrrolidin-2-yl)methyl]-2-methyl-5-sulfamoyl-2,3-dihydro-1-benzofuran-7-carboxamide

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

A suspension of 4.4 g methyl 2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylate and 3.3 g of 1-butyl-2-aminomethylpyrrolidine in 25 ml of diethylene glycol is heated at 120°-130° C. and stirred for 18-20 hours. The reaction solution is cooled to room temperature and added slowly to 150 ml-200 ml of water while stirring. Under ice-cooling crystals are precipitated thoroughly and collected by suction filtration. The crude crystals are dried and recrystallized from ethyl acetate to give crystals of N-(1-butyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide, m.p. 169.5°-170.5° C.

Workup

  1. temperatureis heated at 120°-130° C.
  2. stirringwhile stirring
  3. temperatureUnder ice-cooling crystals
  4. customare precipitated thoroughly
  5. filtrationcollected by suction filtration
  6. customThe crude crystals are dried
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5596a98b0a8740fcbb799b4a19817e1b
Source dataset
uspto-grants-1986_10
Patent number
US04617314

Reaction notes

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