N,N-Dimethylaniline → 2-Chloropheny ethylthieno[2,3-b]pyridine

HRID 1885196ノート

反応式

HRID 1885196 の反応式
N[C:2]1[C:3](C2C=CC=CC=2Cl)=[C:4]2[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:5]2=[N:6][CH:7]=1.CN(C)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl:29]CCl>>[Cl:29][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:10]1[C:4]2[C:5](=[N:6][CH:7]=[CH:2][CH:3]=2)[S:8][C:9]=1[CH2:11][CH3:12]

参加物

4

反応物 3

HCID 949N,N-DimethylanilineHCID 6344DichloromethaneHCID 197871805-Amino-4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridine

生成物 1

HCID 1317175102-Chloropheny ethylthieno[2,3-b]pyridine

実験手順

To a mixture o 4-acetoxy-3,5-dimethoxycinnamic acid (638 mg), dimethylformamide (2 drops) and tetrahydrofuran (8 ml) was added oxazolyl chloride (0.25 ml). The mixture was stirred at room temperature for one hour and then the solvent was distilled off to obtain 4-acetoxy-3,5-dimethoxycinnamic acid chloride as crystals. To a solution of the crystals in dichloromethane (15 ml) were added 5-amino-4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridine (576 mg) and N,N-dimethylaniline (0.25 ml) with ice cooling. After warming to room temperature, the mixture was stirred for 5 hours, washed in turn with water, aqueous saturated NaHCO3 solution and water, and then dried over MgSO4. The solvent was distilled off and the residue was crystallized from ethanol (729 mg, 67.4%). 5-(4-Acetoxy-3,5-dimethoxycinnamoylamino)-4-(2-chloropheny ethylthieno[2,3-b]pyridine was obtained as colorless prisms by recrystallization from acetone, mp: 133°-135° C.

後処理

  1. washwashed in turn with water, aqueous saturated NaHCO3 solution and water
  2. dry with materialdried over MgSO4
  3. distillationThe solvent was distilled off
  4. customthe residue was crystallized from ethanol (729 mg, 67.4%)

出典と根拠

ORDレコード
ord-0c1e1fc5bb634003acc694085bf38aaf
出典データセット
uspto-grants-1992_09
特許番号
US05143919

反応ノート

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