methyl 4-[(2-butyl-5-formyl-4-iodo-1H-imidazol-1-yl)methyl]-2,3-dichlorobenzoate → methyl 4-[(2-butyl-5-formyl-1H-imidazol-1-yl)methyl]-2,3-dichlorobenzoate

HRID 2081869노트

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HRID 2081869 반응식
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([Cl:24])[C:15]=2[Cl:25])[C:7]([CH:11]=[O:12])=[C:8](I)[N:9]=1)[CH2:2][CH2:3][CH3:4]>[Pd].C(OCC)(=O)C.O>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([Cl:24])[C:15]=2[Cl:25])[C:7]([CH:11]=[O:12])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

5

반응물 1

HCID 19936891methyl 4-[(2-butyl-5-formyl-4-iodo-1H-imidazol-1-yl)methyl]-2,3-dichlorobenzoate

생성물 1

HCID 19936913methyl 4-[(2-butyl-5-formyl-1H-imidazol-1-yl)methyl]-2,3-dichlorobenzoate수율 96%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of 34.2 g (0.069 mol) of methyl 4-[(2-butyl-5-formyl-4-iodo-1H -imidazol-1-yl)methyl]-2,3-dichlorobenzoate and 6.84 g of 10% palladium on carbon in 850 mL of ethyl acetate was shaken under hydrogen at 3 Torr for 1 hour. The mixture was filtered through Celite® and concentrated under vacuum to 300 mL. This solution was washed in turn with 5% sodium carbonate solution, water, and brine and then concentrated to an oil which crystallized on standing. This was dissolved in 25 mL of hot methanol which when cooled gave crystals. The suspension was slowly diluted with water and then filtered to give 24.39 g (96%) of crystals; mp 94°-96° C.

후처리

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationconcentrated under vacuum to 300 mL
  3. washThis solution was washed in turn with 5% sodium carbonate solution, water, and brine
  4. concentrationconcentrated to an oil which
  5. customcrystallized
  6. dissolutionThis was dissolved in 25 mL of hot methanol which when
  7. temperaturecooled
  8. customgave crystals
  9. filtrationfiltered

출처 및 근거

ORD 기록
ord-259297fa7eee41d197ce28e79e904ea4
출처 데이터셋
uspto-grants-1993_02
특허 번호
US05185351

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