Ethoxalyl chloride → HCID 12300651, compound

HRID 1415149Notes

Reaction equation

HRID 1415149 reaction equation
[C:1]1([C:7]([C:24]2[NH:28][N:27]=NN=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][CH2:9][N:10]2[CH2:15][CH:14]3[CH2:16][CH2:17][CH:11]2[CH2:12][CH2:13]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:29][C:30](=[O:36])[C:31]([O:33][CH2:34][CH3:35])=[O:32]>N1C=CC=CC=1>[ClH:29].[C:1]1([C:7]([C:24]2[O:36][C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[N:27][N:28]=2)([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:8][CH2:9][N:10]2[CH2:15][CH:14]3[CH2:16][CH2:17][CH:11]2[CH2:12][CH2:13]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 178420260HCID 178420260, compound

Product 1

HCID 12300651HCID 12300651, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Thus 2,2-diphenyl-4-(2-azabicyclo[2.2.2]oct-2-yl)butyronitrile described in U.S. Pat. No. 3,318,869 is reacted with sodium azide in DMF to provide 5-[1,1-diphenyl-3-(2-azabicyclo[2.2.2]oct-2-yl)propyl]-1H-tetrazole. This tetrazole is reacted with ethyl chloroglyoxylate in pyridine at -6° C to provide ethyl [1,1-diphenyl-3-(2-azabicyclo[2.2.2]oct-2-yl)propyl]-1,3,4-oxadiazole-2-carboxylate hydrochloride. This ester is hydrolysed in aqueous potassium hydroxide to provide 5-[1,1-diphenyl-3-(2-azabicyclo[2.2.2]oct-2-yl)propyl]-1,3,4-oxadiazole-2-carboxylic acid. Heating this acid for 15 minutes in an oil bath at 130°-140° provides 5-[1,1-diphenyl-3-(2-azabicyclo[2.2.2]oct-2-yl)propyl]-1,3,4-oxadiazole. The hydrochloride salt melts at 233°-234.5° C.

Sources & evidence

ORD record
ord-1b14d1e4518546bcafdc9812386911cd
Source dataset
uspto-grants-1977_01
Patent number
US04003904

Reaction notes

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