Reaction equation
[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:12][C:13]1[CH:27]=[CH:26][C:16]([CH:17](Cl)[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1.[Cl-].[Na+]>CN(C)C=O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([CH:17]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[N:2]2[N:3]=[N:4][CH:5]=[N:1]2)=[CH:26][CH:27]=1Participants
Procedure
A mixture of 3.12 g of tetrazole, 26.2 g of potassium carbonate, and 10 g of 4,4'-dichlorobenzhydryl chloride from above in 150 ml of dimethylformamide was heated under a nitrogen atmosphere for 2.5 hours at 85°-90° C. and then overnight at 60°-65° C. The reaction mixture was poured into 1 liter of a saturated aqueous sodium chloride solution which was then extracted twice with 200 ml portions of ethyl acetate. The combined organic extracts were washed three times with a saturated sodium chloride solution, dried over magnesium sulfate, and evaporated to dryness to provide 12.1 g of the crude product as a pale yellow oil. The residue was purified by high pressure liquid chromatography. The primary product which was recovered was 1.1 g of the 2-tetrazole derivative as white crystals when recrystallized from methanol, m.p. 91°-92° C. Mass spectral analysis confirmed that the product had the correct molecular formula (M+ =305) and 13C and 1H NMR NOE experiments confirmed that the primary product was 2-[bis(4-chlorophenyl)methyl]-2H-tetrazole.
Workup
- temperaturewas heated under a nitrogen atmosphere for 2.5 hours at 85°-90° C.
- customovernight
- customat 60°-65° C
- extractionwas then extracted twice with 200 ml portions of ethyl acetate
- washThe combined organic extracts were washed three times with a saturated sodium chloride solution
- dry with materialdried over magnesium sulfate
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-5c3073303b824f4fa90995db3d019beb
- Source dataset
- uspto-grants-1989_07
- Patent number
- US04845227
Linked notes
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