Sodium Bicarbonate → N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-methyl-5-t-butylaminosulfonamidobenzamide

HRID 1702942ノート

反応式

HRID 1702942 の反応式
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10](=[O:21])[C:11]1[CH:16]=[C:15]([NH2:17])[C:14]([CH3:18])=[CH:13][C:12]=1[O:19][CH3:20])[CH3:2].[C:22]([NH:26][S:27](Cl)(=[O:29])=[O:28])([CH3:25])([CH3:24])[CH3:23].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(N(CC)CC)C>[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10](=[O:21])[C:11]1[CH:16]=[C:15]([NH:17][S:27]([NH:26][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:29])=[O:28])[C:14]([CH3:18])=[CH:13][C:12]=1[O:19][CH3:20])[CH3:2]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 12682606N-tert-butylsulfamoyl chlorideHCID 53707869N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-methyl-5-aminobenzamide

生成物 1

HCID 12848767N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-methyl-5-t-butylaminosulfonamidobenzamide収率 68.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒3 回HCID 8471Triethylamine溶媒

実験手順

To a mixture of N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-methyl-5-aminobenzamide (1.0 g), dry methylene chloride (20 ml), and triethylamine (693 mg) is added dropwise a mixture of t-butylaminosulfonyl chloride (707 mg) and methylene chloride (5 ml) with ice cooling and stirring. After stirring for 15 minutes, the reaction mixture is mixed with aqueous sodium hydrogencarbonate and shaken with methylene chloride. The organic layer is washed with water, dried over sodium sulfate, and evaporated to remove the solvent. The residue is chromatographed on a column of alumina and eluted with 0-2% methanol/methylene chloride. The eluate is recrystallized from ethyl acetate/isopropyl ether to give N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-4-methyl-5-t-butylaminosulfonamidobenzamide (1.0 g) as crystals melting at 167° to 168° C.

後処理

  1. additionis added dropwise
  2. stirringAfter stirring for 15 minutes
  3. washThe organic layer is washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue is chromatographed on a column of alumina
  8. washeluted with 0-2% methanol/methylene chloride
  9. customThe eluate is recrystallized from ethyl acetate/isopropyl ether

出典と根拠

ORDレコード
ord-73bec68a2c0844ebb018e9ff81068188
出典データセット
uspto-grants-1982_09
特許番号
US04350635

反応ノート

読み込み中…