2-Chloro-1,3-oxazole → 4-Acetoxy-3,5-dimethoxycinnamic acid chloride

HRID 1657220노트

반응식

HRID 1657220 반응식
[C:1]([O:4][C:5]1[C:15]([O:16][CH3:17])=[CH:14][C:8]([CH:9]=[CH:10][C:11](O)=[O:12])=[CH:7][C:6]=1[O:18][CH3:19])(=[O:3])[CH3:2].O1C=CN=C1[Cl:25]>CN(C)C=O.O1CCCC1>[C:1]([O:4][C:5]1[C:15]([O:16][CH3:17])=[CH:14][C:8]([CH:9]=[CH:10][C:11]([Cl:25])=[O:12])=[CH:7][C:6]=1[O:18][CH3:19])(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 133710742-Chloro-1,3-oxazoleHCID 536614803-[4-(Acetyloxy)-3,5-dimethoxyphenyl]prop-2-enoic acid

생성물 1

HCID 541137424-Acetoxy-3,5-dimethoxycinnamic acid chloride

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of 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-chlorophenyl)-2-ethylthieno[2,3-b]pyridine was obtained as colorless prisms by recrystallization from acetone, mp: 133°-135° C.

후처리

  1. distillationthe solvent was distilled off

출처 및 근거

ORD 기록
ord-6b3f28859a7b4293b35a79a4fe013ba6
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05256782

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