Dimethylformamide → 5-Methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzamide

HRID 1791540ノート

反応式

HRID 1791540 の反応式
Cl.[CH3:2][O:3][C:4]1[C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:6][C:7]([N+:13]([O-:15])=[O:14])=[C:8]([CH:12]=1)[C:9](O)=[O:10].C[N:26](C=O)C>S(Cl)(Cl)=O>[CH3:2][O:3][C:4]1[C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:6][C:7]([N+:13]([O-:15])=[O:14])=[C:8]([CH:12]=1)[C:9]([NH2:26])=[O:10]

参加物

4

反応物 2

HCID 6228DimethylformamideHCID 684411845-Methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzoic acid hydrochloride

生成物 1

HCID 218748225-Methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzamide収率 73%

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

実験手順

A solution of 5-methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzoic acid hydrochloride (9.63 g, 24 mmol) in thionyl chloride (20 ml) and DMF (50 μl) was heated at 45° C. for 1.5 hours. The excess thionyl chloride was removed by evaporation and by azeotroping with toluene (×2). The resulting solid was suspended in THF (250 ml) and methylene chloride (100 ml) and ammonia was bubbled though the mixture for 30 minutes and the mixture stirred for a further 1.5 hours at ambient temperature. The volatiles were removed by evaporation, the residue was dissolved in water and applied to a Diaion (trade mark of Mitsubishi) HP20SS resin column and eluted with water/methanol (100/0 to 95/5). The solvent was removed by evaporation from the fractions containing product and the residue was dissolved in a minimum of methanol and the solution was diluted with ether. The resulting precipitate was collected by filtration, washed with ether and dried under vacuum to give 5-methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzamide (7.23 g, 73%).

後処理

  1. customThe excess thionyl chloride was removed by evaporation
  2. customby azeotroping with toluene (×2)
  3. custommethylene chloride (100 ml) and ammonia was bubbled though the mixture for 30 minutes
  4. customThe volatiles were removed by evaporation
  5. dissolutionthe residue was dissolved in water
  6. washeluted with water/methanol (100/0 to 95/5)
  7. customThe solvent was removed by evaporation from the fractions
  8. additioncontaining product
  9. dissolutionthe residue was dissolved in a minimum of methanol
  10. additionthe solution was diluted with ether
  11. filtrationThe resulting precipitate was collected by filtration
  12. washwashed with ether
  13. customdried under vacuum

出典と根拠

ORDレコード
ord-9f93506979e14002b2e5ba7689e3e458
出典データセット
uspto-grants-2006_07
特許番号
US07074800B1

反応ノート

読み込み中…