1,5-Dimethyltetrazole → HCID 13474398, compound

HRID 542802Notes

Reaction equation

HRID 542802 reaction equation
C([Li])CCC.[CH3:6][N:7]1[C:11]([CH3:12])=[N:10][N:9]=[N:8]1.[F:13][C:14]([F:28])([F:27])[C:15]1[CH:26]=[CH:25][C:18]2[C:19](=O)[O:20]C(=O)[NH:22][C:17]=2[CH:16]=1>CCCCCC.O1CCCC1>[NH2:22][C:17]1[CH:16]=[C:15]([C:14]([F:13])([F:27])[F:28])[CH:26]=[CH:25][C:18]=1[C:19](=[O:20])[CH2:12][C:11]1[N:7]([CH3:6])[N:8]=[N:9][N:10]=1

Participants

6

Reactant 3

HCID 788251,5-DimethyltetrazoleHCID 115795307-(Trifluoromethyl)-1H-benzo[d][1,3]oxazine-2,4-dioneHCID 178418339Butyllithium

Product 1

HCID 13474398HCID 13474398, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of butyl lithium in hexane (2.7M, 11.1 ml) was added during 2 minutes to a stirred solution of 1,5-dimethyltetrazole (2.94 g) in dry tetrahydrofuran (100 ml) at -10° to -5°. After stirring for 15 minutes, 7-trifluoromethyl-1H-3,1-benzoxazine-2,4-dione (2.3 g) was added during 5 minutes at -10° to -5°. The reaction mixture was stirred at ambient temperature for 1 hour. Industrial methylated spirit (2 ml) was added and the mixture kept at ambient temperature for 1.5 hours. The mixture was evaporated to one quarter volume, then poured on to ice. The mixture was acidified to pH 2 with hydrochloric acid (5N). The solid product was collected, dried and recrystallised from ethyl acetate:diethyl ether to give the novel compound 1-(2-amino-4-trifluoromethylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone, m.p. 200°-201°.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 1 hour
  2. waitthe mixture kept at ambient temperature for 1.5 hours
  3. customThe mixture was evaporated to one quarter volume
  4. additionpoured on to ice
  5. customThe solid product was collected
  6. customdried
  7. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-cb306b71a9a8429ca724d71d35b23405
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

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