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Potassium Carbonate → 3,5-dihydro-5-(diphenylmethylene)-2-propyl-3-[(2'-(triphenyl methyl tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl]-4H-imidazol-4-one

HRID 21840
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HRID 21840 반응식
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C:10]1[NH:11][C:12](=[O:28])[C:13](=[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:14]=1)[CH2:8][CH3:9].Br[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[CH:43]2[N:47]([CH3:48])[N:46]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[N:45]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[N:44]2[C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[CH:33][CH:32]=1>CN(C)C=O.C(Cl)Cl>[C:22]1([C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:13]2[N:14]=[C:10]([CH2:7][CH2:8][CH3:9])[N:11]([CH2:30][C:31]3[CH:32]=[CH:33][C:34]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[CH:43]4[N:47]([CH3:48])[N:46]([C:49]5[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=5)[N:45]([C:55]5[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=5)[N:44]4[C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)=[CH:35][CH:36]=3)[C:12]2=[O:28])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 543607154'-Bromomethyl-2-(triphenyl methyl tetrazol-5-yl)biphenylHCID 135710997HCID 135710997, 화합물

생성물 1

HCID 199334743,5-dihydro-5-(diphenylmethylene)-2-propyl-3-[(2'-(triphenyl methyl tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl]-4H-imidazol-4-one수율 43.2%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 6344Dichloromethane용매

실험 절차

A mixture of potassium carbonate (83 mg, 2 eq.), 2-propyl-4-(diphenylmethylene)-1H-imidazol-5(4H)-one (90 mg, 0.3 mmol), and 4'-bromomethyl-2-(triphenyl methyl tetrazol-5-yl)biphenyl (0.21 g, 1.2 eq.) in dimethyl formamide (10 mL) was allowed to stir at room temperature for 2 days. The solvent was in vacuo, the residue was dissolved in CH2Cl2 and washed with water and brine. The organic layer was dried over MgSO4 and concentrated. The crude mixture was chromatographed over silica gel eluting with ethyl acetate-hexane (1:4) to give 3,5-dihydro-5-(diphenylmethylene)-2-propyl-3-[(2'-(triphenyl methyl tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl]-4H-imidazol-4-one (100 mg). M.S. m/e 767 (M+ +H) NMR (CDCl3 /TMS) δ0.90 (m, 3H, CH3), 1.65 (m, 2H, CH2), 2.38 (m, 2H, CH2), 4.62 (s, 2H, CH2), 6.88-7.50 (m, 30H, Harom), 7.61 (m, 2H, Harom), 7.90 (d, 1H, Harom). The above compound was detritylated following the procedure described in Example 2C, to give 61 mg of the desired product. M.S. m/e 524 (M+ +H) NMR (CDCl3 /TMS) d 1.01 (t, 3H, CH3), 1.78 (m, 2H, CH2), 2.49 (t, 2H, CH2), 4.75 (s, 2H, CH2), 7.12-7.41 (m, 15H, Harom), 7.58 (m,2H, Harom), 8.10 (d, 1H, Harom).

후처리

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude mixture was chromatographed over silica gel eluting with ethyl acetate-hexane (1:4)

출처 및 근거

ORD 기록
ord-4ffe474de3334a7abc8c52e2c5bbc6b6
출처 데이터셋
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05424450

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