氯甲脒盐酸盐 → 2,4-Diamino-5-methyl-6-[1-chloro-2-(4-trifluoromethylphenyl)ethenyl]quinazoline

HRID 1734603笔记

反应方程式

HRID 1734603 反应方程式
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[C:6]([CH3:22])[C:3]=1[C:4]#[N:5].[ClH:23].Cl[C:25]([NH2:27])=[NH:26]>COCCOCCOC.C(OCC)C>[NH2:27][C:25]1[N:26]=[C:4]([NH2:5])[C:3]2[C:2](=[CH:9][CH:8]=[C:7]([C:10]([Cl:23])=[CH:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=3)[C:6]=2[CH3:22])[N:1]=1

参与物

5

反应物 2

HCID 3084509氯甲脒盐酸盐HCID 541158512-Amino-6-methyl-5-[(4-trifluoromethylphenyl)ethynyl]benzonitrile

产物 1

HCID 537897802,4-Diamino-5-methyl-6-[1-chloro-2-(4-trifluoromethylphenyl)ethenyl]quinazoline收率 46.9%

试剂、催化剂与溶剂 2

HCID 3283乙醚溶剂HCID 8150Diglyme溶剂

实验过程

This compound was prepared in a manner analogous to that of Step E of Example 1, using 2.7 grams (0.009 mole) of 2-amino-6-methyl-5-[(4-trifluoromethylphenyl)ethynyl]benzonitrile and 1.2 grams (0.011 mole) of chloroformamidine hydrochloride in 10 mL of 2-methoxyethyl ether. Upon completion of the reaction, the reaction mixture was diluted with 200 mL of diethyl ether. The resultant solid was collected by filtration, and was dissolved in a hot mixture of 300 mL of water and 100 mL of n-propanol. The solution was filtered hot through a sintered glass funnel to remove some insoluble material. The filtrate was then made basic with 100 mL of concentrated ammonium hydroxide. The resultant solid was collected by filtration, and dried at 60° C. under vacuum. The solid was then dissolved in a solution of 10% methanol in methylene chloride, and the solution was subjected to column chromatography on silica gel. Elution was accomplished using 10% methanol in methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 1.6 grams of 2,4-diamino-5-methyl-6-[1-chloro-2-(4-trifluoromethylphenyl)ethenyl]quinazoline, mp >300° C. The NMR spectrum was consistent with the proposed structure.

后处理

  1. customThis compound was prepared in a manner analogous to that of Step E of Example 1
  2. customUpon completion of the reaction
  3. filtrationThe resultant solid was collected by filtration
  4. dissolutionwas dissolved in a hot mixture of 300 mL of water and 100 mL of n-propanol
  5. filtrationThe solution was filtered hot through a sintered glass funnel
  6. customto remove some insoluble material
  7. filtrationThe resultant solid was collected by filtration
  8. customdried at 60° C. under vacuum
  9. dissolutionThe solid was then dissolved in a solution of 10% methanol in methylene chloride
  10. washElution
  11. concentrationconcentrated under reduced pressure

来源与证据

ORD记录
ord-54fcfbfbcaf54dbfbc5d64d2135b01cc
来源数据集
uspto-grants-1996_07
专利号
US05534518

反应笔记

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