1,5-Dimethyltetrazole → HCID 14723982, compound

HRID 1195369Notes

Reaction equation

HRID 1195369 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 2.2M 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-c79db3c6e321415fb21100819ddefe95
Source dataset
uspto-grants-1992_05
Patent number
US05110940

Reaction notes

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