Potassium Carbonate → 4-[2-(2-Methyl-5-oxo-4,4-diphenyl4,5-dihydro-imidazol-1-yl)-acetyl]-benzoic acid ethyl ester

HRID 507398

반응식

HRID 507398 반응식
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12]Br)=[CH:7][CH:6]=1)[CH3:2].[CH3:16][C:17]1[NH:21][C:20](=[O:22])[C:19]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:18]=1.C(=O)([O-])[O-].[K+].[K+].C1CCCCC1.C(OCC)(=O)C>CC(C)=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12][N:21]2[C:20](=[O:22])[C:19]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:18]=[C:17]2[CH3:16])=[CH:7][CH:6]=1)[CH3:2]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 6195032-methyl-4,4-diphenyl-1H-imidazol-5-oneHCID 11966043Ethyl 4-(2-bromoacetyl)benzoateHCID 21867204Cyclohexane ethylacetate

생성물 1

HCID 684640534-[2-(2-Methyl-5-oxo-4,4-diphenyl4,5-dihydro-imidazol-1-yl)-acetyl]-benzoic acid ethyl ester수율 48.1%

시약·촉매·용매 2

HCID 180Acetone용매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

To a mixture of 4-(2-bromo-acetyl)-benzoic acid ethyl ester (812 mg, 3 mmol) and 2-methyl-5,5-diphenyl-3,5-dihydro-imidazol-4-one (750 mg, 3 mmol) in 12 mL acetone, potassium carbonate (502 mg, 3.6 mmol) is added and the reaction mixture is heated at 70° C. for 5 min in the microwave oven (Biotage Initiator). The mixture is cooled to room temperature, filtered and the filtrate evaporated to yield the crude product which is subjected to flash chromatography. ISCO Companion CombiFlash, 80 g silica gel, cyclohexane/ethyl acetate, gradient, ethyl acetate 0-100% to yield 4-[2-(2-methyl-5-oxo-4,4-diphenyl4,5-dihydro-imidazol-1-yl)-acetyl]-benzoic acid ethyl ester (635 mg, 45%) as light yellow solid. LC/MS at 254 nm; [M+H] 441; Rt 3.613 min.

후처리

  1. additionis added
  2. temperatureThe mixture is cooled to room temperature
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. customto yield the crude product which

출처 및 근거

ORD 기록
ord-f9d8a6508a3d42dbae724ee41ebb2115
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786155B2

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