1,5-Dimethyltetrazole → HCID 13474399, compound

HRID 542804Notes

Reaction equation

HRID 542804 reaction equation
C([Li])CCC.[CH3:6][N:7]1[C:11]([CH3:12])=[N:10][N:9]=[N:8]1.[Br: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]([Br: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 115215774-Bromoisatoic anhydrideHCID 178418339Butyllithium

Product 1

HCID 13474399HCID 13474399, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of butyl lithium in hexane (2.7M, 104 ml) was added slowly to a stirred solution of 1,5-dimethyltetrazole (27.5 g) in dry tetrahydrofuran (500 ml) at -5° to 0° under nitrogen. After stirring for 1.5 hours, 7-bromo-1H-3,1-benzoxazine-2,4-dione (22.6 g) was added and stirring continued for 18 hours at room temperature and for 3.5 hours at 40° to 50°. The mixture was cooled to room temperature, industrial methylated spirit (15 ml) added and most of the solvents distilled off. The residue was added to water (200 ml) and acidified with 5N hydrochloric acid to pH 1. The resulting solid was collected by filtration and crystallised from ethyl acetate to give the novel compound 1-(2-amino-4-bromophenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone, m.p. 159°-160°.

Workup

  1. stirringstirring
  2. waitcontinued for 18 hours at room temperature and for 3.5 hours at 40° to 50°
  3. distillationdistilled off
  4. additionThe residue was added to water (200 ml)
  5. filtrationThe resulting solid was collected by filtration
  6. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-7a35137551014d39bbaffe7281b08038
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

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