1,5-Dimethyltetrazole → HCID 13474397, compound

HRID 542800Notes

Reaction equation

HRID 542800 reaction equation
C([Li])CCC.[CH3:6][N:7]1[C:11]([CH3:12])=[N:10][N:9]=[N:8]1.[CH3:13][C:14]1[CH:25]=[CH:24][C:17]2[C:18](=O)[O:19]C(=O)[NH:21][C:16]=2[CH:15]=1>CCCCCC.O1CCCC1>[NH2:21][C:16]1[CH:15]=[C:14]([CH3:13])[CH:25]=[CH:24][C:17]=1[C:18](=[O:19])[CH2:12][C:11]1[N:7]([CH3:6])[N:8]=[N:9][N:10]=1

Participants

6

Reactant 3

HCID 788251,5-DimethyltetrazoleHCID 124257907-Methyl-2H-3,1-benzoxazine-2,4(1H)-dioneHCID 178418339Butyllithium

Product 1

HCID 13474397HCID 13474397, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of butyl lithium in hexane (2.5M, 20 ml) was added slowly to a stirred solution of 1,5-dimethyltetrazole (4.9 g) in dry tetrahydrofuran (100 ml) at -5° to 0° under nitrogen. After stirring for 0.5 hour, 7-methyl-1H-3,1-benzoxazine-2,4-dione (2.6 g) was added and stirring continued for 1.5 hours at room temperature and for 3 hours at 40°. The solvent was evaporated under reduced pressure at 40°-50°, water (100 ml) was added to the residue, followed by 5N hydrochloric acid dropwise until neutral to Universal pH paper. The mixture was extracted with ethyl acetate (3×50 ml) and the combined extracts were washed with 10% aqueous potassium carbonate solution (50 ml), dried over anhydrous magnesium sulphate and then evaporated under reduced pressure at 50°. The residue was triturated with ether to give a solid product which was collected by filtration and recrystallised from ethyl acetate to give the novel compound 1-(2-amino-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone, m.p. 155°-6°.

Workup

  1. stirringstirring
  2. waitcontinued for 1.5 hours at room temperature and for 3 hours at 40°
  3. customThe solvent was evaporated under reduced pressure at 40°-50°
  4. additionwater (100 ml) was added to the residue
  5. extractionThe mixture was extracted with ethyl acetate (3×50 ml)
  6. washthe combined extracts were washed with 10% aqueous potassium carbonate solution (50 ml)
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated under reduced pressure at 50°
  9. customThe residue was triturated with ether
  10. customto give a solid product which
  11. filtrationwas collected by filtration
  12. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-aaca326ee4b348598696d0ec01436b60
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

Loading…