Hydrochloric Acid → HCID 20207248, compound

HRID 542814Notes

Reaction equation

HRID 542814 reaction equation
C([Li])CCC.[CH3:6][N:7]1[C:11]([CH3:12])=[N:10][N:9]=[N:8]1.[CH2:13]([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)[CH3:14].Cl.[OH-].[Na+]>CCCCCC.O1CCCC1.O>[NH2:22][C:17]1[CH:16]=[C:15]([CH2:13][CH3:14])[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

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 788251,5-DimethyltetrazoleHCID 20207261HCID 20207261, compoundHCID 178418339Butyllithium

Product 1

HCID 20207248HCID 20207248, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of butyl lithium in hexane (2.7M, 13.4 ml) was added to a solution of 1,5-dimethyltetrazole (3.54 g) in dry tetrahydrofuran (83 ml) at 0° under nitrogen. The mixture was stirred for 0.5 hour and 7-ethyl-1H-3,1-benzoxazine-2,4-dione (2.3 g) was added. The mixture was allowed to warm to room temperature during 2 hours. Water (100 ml) was added. The mixture was acidified to pH 1 with hydrochloric acid (5N) and then neutralised with aqueous sodium hydroxide (5N). The mixture was extracted with dichloromethane (2×100 ml). The extract was dried and evaporated. The residue was purified by flash chromatography on Kieselgel 60 using dichloromethane:industrial methylated spirit 99:1 as the eluent. This gave the novel compound 1-(2-amino-4-ethylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone in crude form as an oil.

Workup

  1. extractionThe mixture was extracted with dichloromethane (2×100 ml)
  2. customThe extract was dried
  3. customevaporated
  4. customThe residue was purified by flash chromatography on Kieselgel 60 using dichloromethane:industrial methylated spirit 99:1 as the eluent

Sources & evidence

ORD record
ord-92883a7a6564493c9dbfda7be023be8d
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

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