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

HRID 2290584Notes

Reaction equation

HRID 2290584 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.[NH2:29][CH2:30][CH:31]1[CH2:35][CH2:34][CH2:33][N:32]1[CH2:36][CH3:37]>O.C(N(CC)CC)C.CC(C)=O>[CH2:36]([N:32]1[CH2:33][CH2:34][CH2:35][CH:31]1[CH2:30][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:14](=[O:17])(=[O:16])[NH2:15])[CH:9]=1)=[O:13])[CH3:37]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 10928Ethyl chloroformateHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 136908862-Methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid

Product 1

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

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of 6 g of (-)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid [[α]D =-17.04° (dimethylformamide, c=1)] in a mixed solvent of 55 ml of dimethylformamide and 55 ml of acetone is added 5.9 g of triethylamine and the whole is stirred. The system is cooled to 15° C. and 2.7 g of ethyl chlorocarbonate is added dropwise for 10 minutes. After stirring at room temperature for 40-45 minutes, 7.5 g of (+)-2-aminomethyl-1-ethylpyrrolidine is added. The reactant is stirred at room temperature for 20 minutes and allowed to stand overnight. Excess triethylamine and acetone are distilled off under reduced pressure and the residue obtained is poured into 500-600 ml of water while stirring. Precipitated crystals are collected by suction filtration, washed with water and dried. The crude crystals are recrystallized from ethyl acetate to give crystals of N-(1-ethyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide which is an optically active compound and has a m.p. 163°-164° C. and [α]D =+50.815° (dimethylformamide, c=1).

Workup

  1. stirringAfter stirring at room temperature for 40-45 minutes
  2. stirringThe reactant is stirred at room temperature for 20 minutes
  3. distillationExcess triethylamine and acetone are distilled off under reduced pressure
  4. customthe residue obtained
  5. stirringwhile stirring
  6. customPrecipitated crystals
  7. filtrationare collected by suction filtration
  8. washwashed with water
  9. customdried
  10. customThe crude crystals are recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f2ddfcad95ba46868d918edfe744a523
Source dataset
uspto-grants-1986_10
Patent number
US04617314

Reaction notes

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