Hydrochloric Acid → HCID 70448801, compound

HRID 2290588Notes

Reaction equation

HRID 2290588 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]2[CH:7]=[C:8]([S:14](=[O:18])(=[O:17])[NH:15][CH3:16])[CH:9]=[C:10]([C:11]([OH:13])=O)[C:4]=2[O:3]1.C([Cl:24])(=O)OCC.[CH2:25]([N:27]1[CH2:31][CH2:30][CH2:29][CH:28]1[CH2:32][NH2:33])[CH3:26].Cl>CN(C)C=O.CC(C)=O.C(N(CC)CC)C.C(Cl)(Cl)Cl>[ClH:24].[CH2:25]([N:27]1[CH2:31][CH2:30][CH2:29][CH:28]1[CH2:32][NH:33][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:18])(=[O:17])[NH:15][CH3:16])[CH:9]=1)=[O:13])[CH3:26]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 13690889HCID 13690889, compound

Product 1

HCID 70448801HCID 70448801, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

2-Methyl-5-methylsulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid, 5.0 g, is dissolved in a mixed solvent of 50 ml of dimethylformamide and 50 ml of acetone, 5.7 ml of triethylamine is added and the solution is stirred. Under cooling at 15°-18° C. 2.1 g of ethyl chlorocarbonate is added dropwise for 10 minutes. After stirring at room temperature for 40-45 minutes, 3.0 g of 1-ethyl-2-aminomethylpyrrolidine is added. The reactant is stirred at room temperature for 20 minutes and allowed to stand for 15 hours. Then, excess triethylamine and acetone are distilled off, and the resulting residue is poured into 400 ml of water and extracted with ethyl acetate three times. The ethyl acetate extract layer is washed with water and dried and the ethyl acetate is distilled off under reduced pressure. The residue obtained is dissolved in chloroform and hydrochloric acid gas is blown into the solution. Excess hydrochloric acid gas and chloroform are distilled off under diminished pressure. The resulting residue is crystallized from isopropanol/methanol (3/1) to give crystals of N-(1-ethyl-2-pyrrolidinylmethyl)-2-methyl-5-methylsulfamoyl-2,3-dihydrobenzofuran-7-carboxamide hydrochloride, m.p. 202°-205° C.

Workup

  1. additionis added
  2. temperatureUnder cooling at 15°-18° C
  3. stirringAfter stirring at room temperature for 40-45 minutes
  4. stirringThe reactant is stirred at room temperature for 20 minutes
  5. distillationThen, excess triethylamine and acetone are distilled off
  6. additionthe resulting residue is poured into 400 ml of water
  7. extractionextracted with ethyl acetate three times
  8. extractionThe ethyl acetate extract layer
  9. washis washed with water
  10. customdried
  11. distillationthe ethyl acetate is distilled off under reduced pressure
  12. customThe residue obtained
  13. distillationExcess hydrochloric acid gas and chloroform are distilled off under diminished pressure
  14. customThe resulting residue is crystallized from isopropanol/methanol (3/1)

Sources & evidence

ORD record
ord-1773a32a76f94e70a37ac6c4d16f8661
Source dataset
uspto-grants-1986_10
Patent number
US04617314

Reaction notes

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