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

HRID 2290581Notes

Reaction equation

HRID 2290581 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:21]1[CH2:25][CH2:24][CH2:23][CH:22]1[CH2:26][NH2:27])[CH3:20].O>C(O)COCCO>[CH2:19]([N:21]1[CH2:25][CH2:24][CH2:23][CH:22]1[CH2:26][NH:27][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])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 13420574Methyl 2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylate

Product 1

HCID 13420575N-(1-ethyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

A suspension of 10 g of methyl 2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylate and 7.0 g of 1-ethyl-2-aminomethylpyrrolidine in 50 ml of diethylene glycol is heated at 120°-130° C. and stirred for 18 hours. The reactant solution is cooled to room temperature and added slowly with stirring to 300-400 ml of water. Under ice-cooling crystals are thoroughly deposited. The crude crystals are collected by suction filtration and washed with cold water. The crude crystals obtained are dried and recrystallized from about 220-230 ml of ethyl acetate by the use of decolorizing charcoal to give crystals of N-(1-ethyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide, m.p. 167°-169° C.

Workup

  1. temperatureis heated at 120°-130° C.
  2. additionadded slowly
  3. temperatureUnder ice-cooling crystals
  4. filtrationThe crude crystals are collected by suction filtration
  5. washwashed with cold water
  6. customThe crude crystals obtained
  7. customare dried
  8. customrecrystallized from about 220-230 ml of ethyl acetate by the use of decolorizing charcoal

Sources & evidence

ORD record
ord-0d92c9f9d5ad4d19a6e3a1091d7446ff
Source dataset
uspto-grants-1986_10
Patent number
US04617314

Reaction notes

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