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

HRID 2290583ノート

反応式

HRID 2290583 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.C(N(CC)CC)C.C(Cl)(=O)OCC.[CH2:31]([N:33]1[CH2:37][CH2:36][CH2:35][CH:34]1[CH2:38][NH2:39])[CH3:32]>CN(C)C=O.CC(C)=O>[CH2:31]([N:33]1[CH2:37][CH2:36][CH2:35][CH:34]1[CH2:38][NH:39][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])[CH3:32]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 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 2

HCID 180Acetone溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
15 °C

実験手順

(+)-2-Methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid [[α]D =+16.67° (dimethylformamide, c=1)], 6 g, is dissolved in a mixed solvent of 55 ml of dimethylformamide and 55 ml of acetone and 5.9 g of triethylamine is added, and the whole is stirred. Under cooling at 15° C. 2.7 g of ethyl chlorocarbonate is added dropwise for 10 minutes and the solution is stirred at room temperature for 40-45 minutes. Then, (-)-1-ethyl-2-aminomethylpyrrolidine, 7.5 g, is added and 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 resulting residue is poured while stirring into 500-600 ml of water. Precipitated cystals are separated by suction filtration, washed with water and dried. The filtrate, aqueous layer is extracted with ethyl acetate three times. The extract layer is washed with water and dried, and ethyl acetate is distilled off under reduced pressure to give crude crystals. Both the crude crystals are put together and recrystallized from ethyl acetate to afford crystals of N-(1-ethyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide, m.p. 164°-165° C., [α]D =-50.867° (dimethylformamide, c=1), which is an optically active compound.

後処理

  1. additionis added
  2. stirringthe solution is stirred at room temperature for 40-45 minutes
  3. stirringthe reactant is stirred at room temperature for 20 minutes
  4. distillationExcess triethylamine and acetone are distilled off under reduced pressure
  5. additionthe resulting residue is poured
  6. stirringwhile stirring into 500-600 ml of water
  7. customPrecipitated cystals are separated by suction filtration
  8. washwashed with water
  9. customdried
  10. extractionThe filtrate, aqueous layer is extracted with ethyl acetate three times
  11. washThe extract layer is washed with water
  12. customdried
  13. distillationethyl acetate is distilled off under reduced pressure
  14. customto give crude crystals
  15. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-ebe413b3bcf54a26939186df3746b27c
出典データセット
uspto-grants-1986_10
特許番号
US04617314

反応ノート

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