2-Aminobenzoxazole → HCID 178515424, compound

HRID 1632480Notes

Reaction equation

HRID 1632480 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[NH:11]1[C:15]([CH2:16][C:17]([O:19]CC)=O)=[N:14][N:13]=[N:12]1.[CH:22](OCC)(OCC)OCC.[Cl-].[Cl-].[Cl-].[Al+3]>ClC(Cl)C(Cl)Cl>[NH:14]1[C:15]([C:16]2[C:17](=[O:19])[N:6]3[C:2]([O:3][C:4]4[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=43)=[N:1][CH:22]=2)=[N:11][N:12]=[N:13]1

Participants

6

Reactant 4

HCID 207072-AminobenzoxazoleHCID 31214Ethyl orthoformateHCID 6451240Aluminum(III) ChlorideHCID 178470801HCID 178470801, compound

Product 1

HCID 178515424HCID 178515424, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 65911,1,2,2-TetrachloroethaneSolvent

Procedure

A mixture of 1.34 g (10.0 mmole) of 2-aminobenzoxazole, 1.56 g (10.0 mmole) of ethyl tetrazol-5-ylacetate, 1.65 g (11.1 mmole) of triethyl orthoformate and 0.3 g (2.2 mmole) of aluminum trichloride in 25 ml of 1,1,2,2-tetrachloroethane was heated under a nitrogen atmosphere at 125° to 130° C. for about 19 hours. The mixture was cooled and the resulting solid was separated by filtration and washed with methanol to provide 0.72 g (28%) of crude 3-(1H-tetrazol-5-yl)-4-H-pyrimido[2,1-b]benzoxazol-4-one. Infrared spectral analysis of the crude product confirmed the structural assignment.

Workup

  1. temperaturewas heated under a nitrogen atmosphere at 125° to 130° C. for about 19 hours
  2. temperatureThe mixture was cooled
  3. customthe resulting solid was separated by filtration
  4. washwashed with methanol

Sources & evidence

ORD record
ord-7c7a727e2fd544e6b4cc1ca13c459382
Source dataset
uspto-grants-1984_10
Patent number
US04476130

Reaction notes

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