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

HRID 1885196Notes

Reaction equation

HRID 1885196 reaction equation
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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-0c1e1fc5bb634003acc694085bf38aaf
Source dataset
uspto-grants-1992_09
Patent number
US05143919

Reaction notes

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