Hydrochloric Acid → 1-(2-amino-5-methoxyphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone

HRID 542820

Reaktionsgleichung

Reaktionsgleichung von HRID 542820
C([Li])CCC.[CH3:6][N:7]1[C:11]([CH3:12])=[N:10][N:9]=[N:8]1.[NH2:13][C:14]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:15]=1[C:16](OC)=[O:17].Cl>CCCCCC.O1CCCC1.O>[NH2:13][C:14]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:15]=1[C:16](=[O:17])[CH2:12][C:11]1[N:7]([CH3:6])[N:8]=[N:9][N:10]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 788251,5-DimethyltetrazoleHCID 13052275Methyl 2-amino-5-methoxybenzoateHCID 178418339Butyllithium

Produkt 1

HCID 134744061-(2-amino-5-methoxyphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of butyl lithium in hexane (2.5M, 18.5 ml) was added to a stirred solution of 1,5-dimethyl-tetrazole (4.55 g) in dry tetrahydrofuran (100 ml) at 0°. After 30 minutes methyl 2-amino-5-methoxybenzoate (2.8 g) was added and stirring was continued for 3 hours. The reaction mixture was poured into water (200 ml), acidified with hydrochloric acid (5N) to pH 1, and extracted with dichloromethane (3×100 ml). The extract was dried over anhydrous magnesium sulphate and evaporated. The residue was recrystallised from industrial methylated spirit to give the novel compound 1-(2-amino-5-methoxyphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone, m.p. 170°-172°.

Aufarbeitung

  1. extractionextracted with dichloromethane (3×100 ml)
  2. dry with materialThe extract was dried over anhydrous magnesium sulphate
  3. customevaporated
  4. customThe residue was recrystallised from industrial methylated spirit

Quellen und Nachweise

ORD-Eintrag
ord-047eaa02e81d440bb27f354bc50b6ce5
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659718

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