Sodium Carbonate → Procainamide

HRID 550770

反応式

HRID 550770 の反応式
[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][NH:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=1)=[O:10])[CH2:4][CH3:5].Cl.C([O-])([O-])=O.[Na+].[Na+]>O>[CH3:5][CH2:4][N:3]([CH2:6][CH2:7][NH:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)=[O:10])[CH2:2][CH3:1]

参加物

4

反応物 2

HCID 10340Sodium CarbonateHCID 66068Procainamide Hydrochloride

生成物 1

HCID 4913Procainamide収率 105.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of procainamide hydrochloride (2.5 g) in H2O was treated with 2M aqueous Na2CO3 solution and extracted with EtOAc. The organic phase was washed (2 M aqueous Na2CO3 soln.), dried (Na2SO4), filtered and concentrated to give procainamide (2.28 g) as clear oil. A mixture of the intermediate 5 (100 mg, 0.35 mmol) and Cs2CO3 (174 mg, 0.53 mmol) was treated with a solution of procainamide (125 mg, 0.53 mmol) in dry DMSO (1.2 ml). The mixture was stirred at 100° C. for 5 h, followed by a normal workup (EtOAc, saturated aqueous NaHCO3 solution, saturated aqueous NaCl soln.; Na2SO4). Flash chromatography (eluent: DCM/MeOH gradient then DCM/MeOH gradient containing 1% conc. aqueous NH3 solution) and further purification by preparative TLC (eluent: DCM/MeOH containing 1% concentrated aqueous NH3 solution) gave 20 mg (12.8%) of compound 6.

後処理

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed (2 M aqueous Na2CO3 soln.)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-6c67c72154844d6a8aeb7b44c37a649e
出典データセット
uspto-grants-2011_05
特許番号
US07947694B2

関連ノート

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