Nitric Acid → 2,4-Diamino-5-(3-amino-4-chloro-5-nitrophenyl)-6-ethylpyrimidine

HRID 440980

반응식

HRID 440980 반응식
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[NH2:10][C:11]1[N:16]=[C:15]([NH2:17])[C:14]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:13]([CH2:25][CH3:26])[N:12]=1.[OH-].[NH4+]>>[NH2:10][C:11]1[N:16]=[C:15]([NH2:17])[C:14]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[C:22]([N+:1]([O-:4])=[O:2])[CH:23]=2)=[C:13]([CH2:25][CH3:26])[N:12]=1

참가 물질

5

반응물 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 4993PyrimethamineHCID 14923Ammonium Hydroxide

생성물 1

HCID 3274042,4-Diamino-5-(3-amino-4-chloro-5-nitrophenyl)-6-ethylpyrimidine

반응 조건

온도
50 °C

실험 절차

A stirred solution of 75 mL of 70% nitric acid and 75 mL of concentrated sulfuric acid warmed to about 50° C. from the heat of solution. To this was added 25 grams (0.10 mole) of 2,4-diamino-5-(4-chloro-phenyl)-6-ethylpyrimidine (commercially available) during a 10 minute period. Upon completion of addition, the reaction mixture was stirred at 50° C. for about 1 hour. After this time, the reaction mixture was allowed to cool to ambient temperature where it was stirred for about 18 hours. The reaction mixture was then poured into 1000 mL of ice containing 110 mL of concentrated ammonium hydroxide. The resultant solid was collected by filtration and recrystallized from aqueous ethanol, yielding 29.2 grams of 2,4-diamino-5-(4-chloro-3-nitrophenyl)-6-ethylpyrimidine. The NMR spectrum was consistent with the proposed structure.

후처리

  1. temperatureheat of solution
  2. additionUpon completion of addition
  3. temperatureto cool to ambient temperature where it
  4. stirringwas stirred for about 18 hours
  5. filtrationThe resultant solid was collected by filtration
  6. customrecrystallized from aqueous ethanol

출처 및 근거

ORD 기록
ord-a003a4a9639c4aa3843c4d4c178c4ed4
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521192

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