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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
Notes
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Reaction equation

HRID 21840 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 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-oneYield 43.2%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-4ffe474de3334a7abc8c52e2c5bbc6b6
Source dataset
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05424450

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes