Sodium Hydroxide → HCID 178440045, compound

HRID 21839Notes

Reaction equation

HRID 21839 reaction equation
[C:1]1([C:7](=[C:9]2[N:13]=[C:12]([CH2:14][CH2:15][CH3:16])[N:11]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[N:34](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:33]=[N:32][N:31]=4)=[CH:20][CH:19]=3)[C:10]2=[O:54])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O1CCCC1.Cl>[C:1]1([C:7](=[C:9]2[N:13]=[C:12]([CH2:14][CH2:15][CH3:16])[N:11]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[NH:34][N:33]=[N:32][N:31]=4)=[CH:20][CH:19]=3)[C:10]2=[O:54])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 678057693,5-dihydro-5-(1-phenylethylidene)-2-propyl-3-[(2'-(triphenylmethyltetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl]-4H-imidazol-4-one

Product 1

HCID 178440045HCID 178440045, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

3,5-dihydro-5-(1-phenylethylidene)-2-propyl-3-[(2'-(triphenylmethyltetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl]-4H-imidazol-4-one (0.17 g) in tetrahydrofuran (20 mL) and 10% hydrochloric acid (5 mL) was allowed to stir at room temperature for 3.5 hr. The reaction mixture was treated with 50% sodium hydroxide to pH 8, concentrated and cooled in ice bath. The precipitate was filtered and the aqueous solution was adjusted to pH 4-5 using concentrated hydrochloric acid to give white solid which was washed with cold water and dried to give yellow solid (80 mg) as a mixture of the Z and E isomers (8:2). M.S. m/e 463 (M+ +H) NMR (CDCl3 /TMS) δ0.98 (t, 3H, CH3), 1.67 (m, 2H, CH2), 2.39 (t, 2H, CH2), 2.76 (s, 3H, CH3), 4.80 (s, 2H, CH2), 7.04-7.20 (m, 4H, Harom), 7.42-7.61 (m, 2H, Harom), 7.63 (d, 2H, Harom), 7.99 (d, 1H, Harom).

Workup

  1. concentrationconcentrated
  2. temperaturecooled in ice bath
  3. filtrationThe precipitate was filtered
  4. customto give white solid which
  5. washwas washed with cold water
  6. customdried

Sources & evidence

ORD record
ord-2838af388d24488192a46a8cb6636236
Source dataset
uspto-grants-1995_06
Patent number
US05424450

Reaction notes

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