Salicylamide → 2-[(1-Methyl-3-pyrrolidinyl)oxy]benzamide

HRID 4779

反応式

HRID 4779 の反応式
[NH2-].[Na+].[CH3:3][N:4]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5]1.C1(C)C(S(Cl)(=O)=O)=CC=CC=1.C[O-].[Na+].[C:24]([NH2:33])(=[O:32])[C:25]1[C:26](=[CH:28][CH:29]=[CH:30][CH:31]=1)O>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:3][N:4]1[CH2:8][CH2:7][CH:6]([O:9][C:31]2[CH:30]=[CH:29][CH:28]=[CH:26][C:25]=2[C:24]([NH2:33])=[O:32])[CH2:5]1

参加物

8

反応物 5

HCID 5147SalicylamideHCID 8623o-Toluenesulfonyl chlorideHCID 24533Sodium amideHCID 930741-Methyl-3-pyrrolidinolHCID 10942334Sodium Methoxide

生成物 1

HCID 137262832-[(1-Methyl-3-pyrrolidinyl)oxy]benzamide

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

To 85.6 g (2.2 moles) of sodium amide in 1.5 liter of dry toluene was added 202 g (2 moles) of 1-methyl-3-pyrrolidinol so as not to exceed a temperature of 50° C. The mixture was then heated to 70° C. for 4.5 hours. The mixture was cooled and 381 g (2 moles) of o-toluenesulfonylchloride was added at a rapid drop while maintaining a temperature of 20°-30° C. with an ice bath. The mixture was stirred at room temperature for 2.5 hours and washed with water. The toluene solution was dried with sodium sulfate and concentrated. The residue, dissolved in 500 ml of dimethylformamide, was added to a reaction mixture prepared by adding 119 g (2.2 moles) of sodium methoxide and 274 g (2.0 moles) of salicylamide to one liter of dimethylformamide and the mixture was worked up as in preparation 1. Yield of product was 170 g (38%), m.p. 116°-118° C.

後処理

  1. customa temperature of 50° C
  2. temperatureThe mixture was cooled
  3. temperaturewhile maintaining a temperature of 20°-30° C. with an ice bath
  4. washwashed with water
  5. dry with materialThe toluene solution was dried with sodium sulfate
  6. concentrationconcentrated
  7. dissolutionThe residue, dissolved in 500 ml of dimethylformamide
  8. additionwas added to a reaction mixture
  9. customprepared
  10. customthe mixture was worked up as in preparation 1

出典と根拠

ORDレコード
ord-b0c0fc9ef6e847a68cadcb68fa16fa36
出典データセット
uspto-grants-1988_02
特許番号
US04727152

関連ノート

読み込み中…