1,5-Dimethyltetrazole → HCID 14723982, compound

HRID 2165314Notes

Reaction equation

HRID 2165314 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[N:5][N:4]=[N:3]1.C([Li])CCC.[F:13][C:14]1[CH:29]=[CH:28][C:17]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[CH3:27])=[O:19])=[C:16]([CH3:30])[CH:15]=1>O1CCCC1>[F:13][C:14]1[CH:29]=[CH:28][C:17]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[CH3:27])([OH:19])[CH2:7][C:6]2[N:2]([CH3:1])[N:3]=[N:4][N:5]=2)=[C:16]([CH3:30])[CH:15]=1

Participants

5

Reactant 3

HCID 788251,5-DimethyltetrazoleHCID 14371388HCID 14371388, compoundHCID 178418339Butyllithium

Product 1

HCID 14723982HCID 14723982, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1,5-dimethyltetrazole (3.8 g, 39.0 mmoles) in tetrahydrofuran (40 mL) at -40° C. was added butyl lithium (17.7 mL of a 2.2 M solution, 39.0 mmoles). After stirring for 10 minutes, 4,4'-difluoro-2,2'-dimethylbenzophenone (8 g, 32.5 mmoles) was added and the solution stirred for 3 hours. The reaction was quenched with 1N hydrochloric acid. The aqueous layer was separated and extracted With ethyl acetate. The combined organic phases were dried (MgSO4) and concentrated in vacuo to give 7.5 g of the title compound; m.p.=186°-188° C.

Workup

  1. stirringthe solution stirred for 3 hours
  2. customThe reaction was quenched with 1N hydrochloric acid
  3. customThe aqueous layer was separated
  4. extractionextracted With ethyl acetate
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-551e94b75d7a49ec9a46bded687deca3
Source dataset
uspto-grants-1990_07
Patent number
US04939265

Reaction notes

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