Hydrochloric Acid → HCID 178439996, compound

HRID 1656404Notes

Reaction equation

HRID 1656404 reaction equation
[C:1]1([C:11]2[N:12]=[C:13]([CH2:55][CH2:56][CH3:57])[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]4[N:35](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:34]=[N:33][N:32]=4)=[CH:21][CH:20]=3)[C:15]=2[CH:16]=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl>C1COCC1>[C:1]1([C:11]2[N:12]=[C:13]([CH2:55][CH2:56][CH3:57])[N:14]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]4[NH:35][N:34]=[N:33][N:32]=4)=[CH:23][CH:24]=3)[C:15]=2[CH:16]=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19787719HCID 19787719, compound

Product 1

HCID 178439996HCID 178439996, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Naphth-1-yl)-2-n-propyl-1-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]imidazole-5-carboxaldehyde (1.50 g), THF (80 mL), and 10% HCl were stirred at room temperature. After 8 hr, the mixture was poured into ice/5% NaOH and the pH was adjusted to 10. The resultant solids were filtered and the pH of the filtrate was adjusted to 4-5 with 10% HCl. The turbide solution was extracted with 80/20 methylene chloride/i-propanol (3×100 mL), the organic phase was dried over sodium sulfate and evaporated under reduced pressure to yield 0.51 g of a white glass. NMR (CDCl3) δ 9.35 (s, 1H); 7.78 (m, 1H); 7.60-7.38 (m, 2H); 7.35-6.96 (m, 12H); 5.62 (s, 1H); 2.60 (m, 2H); 1.85 (m, 2H); 0.90 (t, 3H).

Workup

  1. filtrationThe resultant solids were filtered
  2. extractionThe turbide solution was extracted with 80/20 methylene chloride/i-propanol (3×100 mL)
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1000a6220fe3437e90efa3be990915df
Source dataset
uspto-grants-1993_10
Patent number
US05254546

Reaction notes

Loading…