Chloroformamidinium chloride → 2,4-Diamino-5-methyl-6-[1-chloro-2-(4-trifluoromethylphenyl)ethenyl]quinazoline

HRID 363775

반응식

HRID 363775 반응식
[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

참가 물질

5

반응물 2

HCID 3084509Chloroformamidinium chlorideHCID 541158512-Amino-6-methyl-5-[(4-trifluoromethylphenyl)ethynyl]benzonitrile

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8150Diglyme용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f5a5a7a2eaa24d90be44ac378bc0424c
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05874579

연결된 노트

불러오는 중…