Methyl Anthranilate → HCID 178497644, compound

HRID 236397Notes

Reaction equation

HRID 236397 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[N:4][N:3]=1.[CH2:7](OC(OCC)OCC)C.[C:17]([O:26][CH3:27])(=[O:25])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[NH2:20]>CCCCCC>[NH:3]1[C:2]([NH:1][CH:7]=[N:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[C:17]([O:26][CH3:27])=[O:25])=[N:6][N:5]=[N:4]1

Participants

5

Reactant 3

HCID 8635Methyl Anthranilate2×HCID 31214Ethyl orthoformateHCID 178509299HCID 178509299, compound

Product 1

HCID 178497644HCID 178497644, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 5 g of 5-aminotetrazole, 46.7 g of triethoxymethane, 10.5 g of methyl anthranilate and 105 ml of hexane was heated at reflux under nitrogen for 48 hours. The mixture was cooled to room temperature and the white crystalline product was separated by filtration, washed with hexane and vacuum oven dried to give product containing traces of methyl anthranilate. This was triturated with additional hexane, followed by filtration and drying to give pure N1 -(1H-tetrazol-5-yl)-N2 -(2-carbomethoxyphenyl)formamidine.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 48 hours
  3. customthe white crystalline product was separated by filtration
  4. washwashed with hexane and vacuum oven
  5. customdried
  6. customto give product
  7. customThis was triturated with additional hexane
  8. filtrationfollowed by filtration
  9. customdrying

Sources & evidence

ORD record
ord-21e3012bfabd4751bb642c97a0329667
Source dataset
uspto-grants-1987_02
Patent number
US04644065

Reaction notes

Loading…