1H-Tetrazole, 5-chloro-1-phenyl- → HCID 14742759, compound

HRID 1651239Notes

Reaction equation

HRID 1651239 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([OH:16])[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[CH:11][CH:12]=2)[C:7]=1[CH2:19][CH2:20][CH2:21][CH3:22])=[O:5])[CH3:2].Cl[C:24]1[N:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:27]=[N:26][N:25]=1.CC(C)([O-])C.[K+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][C:24]2[N:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:27]=[N:26][N:25]=2)[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[CH:11][CH:12]=2)[C:7]=1[CH2:19][CH2:20][CH2:21][CH3:22])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 14742755HCID 14742755, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14742759HCID 14742759, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

As in Example 132, 1-butyl-4-hydroxy-7-methoxy-2-naphthalenecarboxylic acid ethyl ester (2.9 g) was reacted with 5-chloro-1-phenyl-1H-tetrazole (1.87 g) in dimethylformamide (25 mL) in the presence of potassium t-butoxide (1.25 g). After 0.5 hours at room temperature, the reaction was worked up in the described manner and the crude product was crystallized from diethyl ether-hexane to afford 2.9 g of 1-butyl-7-methoxy-4-[(1-phenyl-1H-tetrazole-5-yl)oxy]-2-naphthalenecarboxylic acid ethyl ester, mp 94°-96° C. A sample was recrystallized from the same solvents to provide the analytical specimen, mp 95.5°-96.5° C. Anal. Calcd for C25H26N4O4 : C, 67.25; H, 5.87; N, 12.55 Found: C, 67.16; H, 5.99; N, 12.66

Workup

  1. customthe crude product was crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-0364619ab19943c09e29ead426f30b2b
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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