1H-Tetrazole, 5-chloro-1-phenyl- → HCID 14742758, compound

HRID 1651233Notes

Reaction equation

HRID 1651233 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:9][C:10]([C:12]1[CH:21]=[C:20]([OH:22])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[O:23][CH3:24])[C:13]=1[CH2:25][CH2:26][CH2:27][CH3:28])=[O:11])[CH3:8].Cl[C:30]1[N:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:33]=[N:32][N:31]=1>CN(C)C=O>[CH2:7]([O:9][C:10]([C:12]1[CH:21]=[C:20]([O:22][C:30]2[N:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:33]=[N:32][N:31]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[O:23][CH3:24])[C:13]=1[CH2:25][CH2:26][CH2:27][CH3:28])=[O:11])[CH3:8]

Participants

5

Reactant 3

HCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 14742754HCID 14742754, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14742758HCID 14742758, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium t-butoxide (1.03 g) was added to a solution of 1-butyl-4-hydroxy-5-methoxy-2-naphthalenecarboxylic acid ethyl ester (2.4 g) and 5-chloro-1-phenyl-1H-tetrazole (1.55 g) in dimethylformamide (20 mL) and the reaction was stirred at room temperature for 1.25 hours. After the solvent was removed in vacuo, the residual material was partitioned between dichloromethane (150 mL) and water (75 mL). The separated aqueous layer was re-extracted with dichloromethane, and after each organic extract was washed with water, they were combined, dried (Na2SO4) and evaporated. Crystallization of the crude product from diethyl ether-hexane gave 2.15 g of 1-butyl-5-methoxy-4-[(1-phenyl-1H-tetrazole-5-yl)oxy]-2-naphthalenecarboxylic acid ethyl ester, mp 144°-146° C. A portion was recrystallized from the same solvents to provide the analytical sample, mp 145°-146° C. Anal. Calcd for C25H26N4O4 : C, 67.25; H, 5.87; N, 12.55 Found: C, 67.07; H, 5.99; N, 12.51

Workup

  1. customAfter the solvent was removed in vacuo
  2. customthe residual material was partitioned between dichloromethane (150 mL) and water (75 mL)
  3. extractionThe separated aqueous layer was re-extracted with dichloromethane
  4. extractionafter each organic extract
  5. washwas washed with water, they
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customCrystallization of the crude product from diethyl ether-hexane

Sources & evidence

ORD record
ord-d97ac595320e4816bc7deae84a94180a
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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