Ethyl orthoformate → methyl 2-methoxy-5-(1H-tetrazol-1-yl)benzoate

HRID 1456326Notes

Reaction equation

HRID 1456326 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10].[CH:18](OCC)(OCC)OCC.N([O-])=O.[Na+]>C(O)(=O)C.CN(C)C=O.O>[CH3:5][O:6][C:7]1[CH:16]=[CH:15][C:14]([N:17]2[CH:18]=[N:3][N:2]=[N:1]2)=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

8

Reactant 4

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 89843Methyl 5-amino-o-anisateHCID 23668193Sodium Nitrite

Product 1

HCID 18464873methyl 2-methoxy-5-(1H-tetrazol-1-yl)benzoate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (0.54 g) was added to a stirred solution of 2-methoxy-5-amino benzoic acid, methyl ester (1 g ) and triethyl orthoformate (1.38 ml) in glacial acetic acid (8 ml) and dimethylformamide (2 ml). The mixture was heated to 79°-80°. After 11/4 h the solution was allowed to cool (ice-water bath) and a solution of sodium nitrite (0.57 g) in water (10 ml) was added slowly. After stirring for 30 min, water (40 ml) was added. After 2 h, the mixture was filtered. The residual white solid was washed with water and dried in vacuo, at 25° to give the title compound (0.83 g); mp 185°-187°.

Workup

  1. temperatureThe mixture was heated to 79°-80°
  2. custom4 h
  3. waitAfter 2 h
  4. filtrationthe mixture was filtered
  5. washThe residual white solid was washed with water
  6. customdried in vacuo, at 25°

Sources & evidence

ORD record
ord-7fc65fc61d484b34af99a7111fb18a67
Source dataset
uspto-grants-1998_12
Patent number
US05843966

Reaction notes

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