Butoxy(oxo)acetate → Tazanolast

HRID 260231Notes

Reaction equation

HRID 260231 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:12][N:11]=[N:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:13]([O:17][C:18](=[O:22])[C:19]([O-])=[O:20])[CH2:14][CH2:15][CH3:16]>>[CH3:16][CH2:15][CH2:14][CH2:13][O:17][C:18]([C:19]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[N:11][NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1)=[O:20])=[O:22]

Participants

3

Reactant 2

HCID 21904025Butoxy(oxo)acetateHCID 178507542HCID 178507542, compound

Product 1

HCID 5380TazanolastYield 75%

Procedure

5-(3-Aminophenyl)tetrazole (1.7 g) was added to 12 ml of n-butyloxalate and reacted at a bath temperature of 165° to 175° C. for 1.5 hr while stirring. After cooling, the precipitated crystals were filtered off and recrystallized from acetone-n-hexane, to give 2.3 g (yield: 75%) of 5-(3-n-butyloxalylaminophenyl)tetrazole.

Workup

  1. customreacted at a bath temperature of 165° to 175° C. for 1.5 hr
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were filtered off
  4. customrecrystallized from acetone-n-hexane

Sources & evidence

ORD record
ord-ab8080aa466f4526aad5d4d3cf1847d5
Source dataset
uspto-grants-1996_06
Patent number
USRE035281

Reaction notes

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