Acetic Acid → 6-[1-(1H-imidazol-1yl)-2-methylpropyl]-3-propyl-2(1H)-quinoxalinone

HRID 1886360노트

반응식

HRID 1886360 반응식
[N:1]1([CH:6]([C:10]2[CH:11]=[C:12]([NH2:17])[C:13]([NH2:16])=[CH:14][CH:15]=2)[CH:7]([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1.C(O)(=O)C.O=[C:23]([CH2:27][CH2:28][CH3:29])[C:24](O)=[O:25].[OH-].[Na+]>O>[N:1]1([CH:6]([C:10]2[CH:11]=[C:12]3[C:13](=[CH:14][CH:15]=2)[NH:16][C:24](=[O:25])[C:23]([CH2:27][CH2:28][CH3:29])=[N:17]3)[CH:7]([CH3:8])[CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 745632-Oxovaleric acidHCID 145184264-[1-(1H-imidazol-1-yl)-2-methylpropyl]-1,2-benzenediamine

생성물 1

HCID 198758996-[1-(1H-imidazol-1yl)-2-methylpropyl]-3-propyl-2(1H)-quinoxalinone

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a stirred and cooled (0° C.) mixture of 9 parts of 4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-1,2-benzenediamine in 80 parts of acetic acid and 20 parts of water were added 5 parts of 2-oxopentanoic acid. The reaction mixture was stirred for 12 hours at room temperature. The whole was poured into ice water and neutralized with a sodium hydroxide solution 3N. The product was extracted three times with 130 parts of dichloromethane. The combined extracts were dried, filtered and evaporated. For obtaining 6-[1-(1H-imidazol-1yl)-2-methylpropyl]-3-propyl-2(1H)-quinoxalinone, the residue was purified by column chromatography (HPLC) over silica gel using a mixture of dichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-butanone and 1,1'-oxybisethane. The precipitated product was filtered off and stirred in cold 4-methyl-2-pentanone. After filtration, the product was recrystallized from a mixture of methanol and 2-propanone, yielding 1.6 parts (13.2%) of the above product; mp. 259.7° C. (comp. 100).

후처리

  1. temperaturecooled
  2. stirringThe reaction mixture was stirred for 12 hours at room temperature
  3. extractionThe product was extracted three times with 130 parts of dichloromethane
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-6c5766da0fb64f90be6fad318be66f3d
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05151421

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