Anthranilic Acid → HCID 178515044, compound

HRID 236401Notes

Reaction equation

HRID 236401 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[N:4][N:3]=1.[CH2:7](OC(OCC)OCC)C.[C:17]([OH:26])(=O)[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[NH2:20].[OH-].[NH4+]>CO.CN(C)C=O>[NH:3]1[C:2]([N:1]2[C:17](=[O:26])[C:18]3[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:20]=[CH:7]2)=[N:6][N:5]=[N:4]1

Participants

7

Reactant 4

HCID 227Anthranilic Acid2×HCID 14923Ammonium HydroxideHCID 31214Ethyl orthoformateHCID 178509299HCID 178509299, compound

Product 1

HCID 178515044HCID 178515044, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture was prepared from 10 g of 5-aminotetrazole and 50 ml N,N-dimethylformamide. This was heated to 100° C. and 17 g of triethoxymethane was added. The resulting mixture was stirred at 100° C. under nitrogen for 2 hours and then a solution of the ammonium salt of anthranilic acid (prepared from 16 g of anthranilic acid and 7.8 ml of 14.8M ammonium hydroxide in methanol, followed by removal of the methanol) in 40 ml of N,N-dimethylformamide was added. The mixture was stirred for 1 hour at 100° C., then cooled to room temperature and finally cooled in an ice bath to induce crystallization. The white crystals which formed were separated by filtration, washed with N,N-dimethylformamide and then with carbon tetrachloride, and vacuum oven dried to give the ammonium salt of 3-(1H-tetrazol-5-yl)4(3H)-quinazolinone.

Workup

  1. customfollowed by removal of the methanol) in 40 ml of N,N-dimethylformamide
  2. additionwas added
  3. stirringThe mixture was stirred for 1 hour at 100° C.
  4. temperaturecooled to room temperature
  5. temperaturefinally cooled in an ice bath
  6. customcrystallization
  7. customThe white crystals which formed
  8. customwere separated by filtration
  9. washwashed with N,N-dimethylformamide
  10. dry with materialwith carbon tetrachloride, and vacuum oven dried

Sources & evidence

ORD record
ord-0f0b9f437c20401e9a74f14fab79aaf8
Source dataset
uspto-grants-1987_02
Patent number
US04644065

Reaction notes

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