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

HRID 2290584ノート

反応式

HRID 2290584 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 8471Triethylamine溶媒

反応条件

温度
15 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f2ddfcad95ba46868d918edfe744a523
出典データセット
uspto-grants-1986_10
特許番号
US04617314

反応ノート

読み込み中…