Hydrochloric Acid → HCID 13474400, compound

HRID 542806Notes

Reaction equation

HRID 542806 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[C:15]([CH3:26])=[CH:16][C:17]2[NH:22]C(=O)[O:20][C:19](=O)[C:18]=2[CH:25]=1.Cl.[OH-].[Na+]>CCCCCC.O1CCCC1.O>[NH2:22][C:17]1[CH:16]=[C:15]([CH3:26])[C:14]([CH3:13])=[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 107028726,7-Dimethyl-2H-3,1-benzoxazine-2,4(1H)-dioneHCID 178418339Butyllithium

Product 1

HCID 13474400HCID 13474400, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of butyl lithium in hexane (2.7M, 9.8 ml) was added to a stirred solution of 1,5-dimethyltetrazole (2.6 g) in dry tetrahydrofuran (25 ml) at 0° under nitrogen. After 1 hour, 6,7-dimethyl-1H-3,1-benzoxazine-2,4-dione (1.69 g) was added and stirring was continued for 4 hours. The mixture was poured into water (200 ml), acidified with hydrochloric acid (5N) to pH 1, neutralised with aqueous sodium hydroxide (5N) and extracted with dichloromethane (3×100 ml). The combined extracts were dried and evaporated under reduced pressure. The residue was triturated with water to give a yellow solid which was collected by filtration and dried to give the novel compound 1-(2-amino-4,5-dimethylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone, m.p. 162°-165°.

Workup

  1. waitwas continued for 4 hours
  2. extractionextracted with dichloromethane (3×100 ml)
  3. customThe combined extracts were dried
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with water
  6. customto give a yellow solid which
  7. filtrationwas collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-4ac70ce0a8754c18bf2cebf84c6f9106
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

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