氢化钠 → 3-(4-chloro-2-nitrophenyl)-6-trifluoromethyl-2,4 (1H, 3H)-pyrimidinedione

HRID 277429

反应方程式

HRID 277429 反应方程式
[H-].[Na+].C(O[C:6](=[O:14])/[CH:7]=[C:8](\[NH2:13])/[C:9]([F:12])([F:11])[F:10])C.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[C:18]([N+:25]([O-:27])=[O:26])[CH:17]=1>CN(C)C=O.C1(C)C=CC=CC=1>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:6](=[O:14])[CH:7]=[C:8]([C:9]([F:10])([F:11])[F:12])[NH:13][C:23]2=[O:24])=[C:18]([N+:25]([O-:27])=[O:26])[CH:17]=1

参与物

6

反应物 3

HCID 24758氢化钠HCID 42472574-氯-2-异氰酸硝基苯HCID 57025293-氨基-4,4,4-三氟巴豆酸乙酯

产物 1

HCID 570852913-(4-chloro-2-nitrophenyl)-6-trifluoromethyl-2,4 (1H, 3H)-pyrimidinedione

试剂、催化剂与溶剂 2

HCID 1140甲苯溶剂2 次HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
-30 °C

实验过程

To a suspension of sodium hydride (60% dispersion in oil, 2.5 g) in anhydrous N,N-dimethylformamide (100 ml) was added dropwise a solution of ethyl-3-amino-4,4,4-trifluorocrotonate in toluene (50 ml) at 0° C. under nitrogen atmosphere. After addition, the mixture was stirred for 20 min at same temperature, then cooled to −30° C. A solution of (4-chloro-2-nitrophenyl)isocyanate in toluene (50 ml) was added dropwise. After stirring for 20 min, the cold bath was removed and the resulting mixture was stirred overnight at ambient temperature. The reaction mixture was partitioned between ethyl acetate and 1N-hydrochloric acid. The organic phase was washed with brine (×2) and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel eluted with ethyl acetate and hexane (1:1) to afford 3-(4-chloro-2-nitrophenyl)-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (10.2 g) as a yellow solid.

后处理

  1. additionAfter addition
  2. stirringAfter stirring for 20 min
  3. customthe cold bath was removed
  4. stirringthe resulting mixture was stirred overnight at ambient temperature
  5. customThe reaction mixture was partitioned between ethyl acetate and 1N-hydrochloric acid
  6. washThe organic phase was washed with brine (×2)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by column chromatography on silica gel
  10. washeluted with ethyl acetate and hexane (1:1)

来源与证据

ORD记录
ord-b8af29faa372412783beaf9f44a95f85
来源数据集
uspto-grants-2002_03
专利号
US06355799B1

关联笔记

加载中…