Methyl Anthranilate → HCID 178497644, compound

HRID 236396Notes

Reaction equation

HRID 236396 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]>CN(C)C=O>[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 AnthranilateHCID 31214Ethyl orthoformateHCID 178509299HCID 178509299, compound

Product 1

HCID 178497644HCID 178497644, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture was prepared from 9.5 g of 5-aminotetrazole, 16.5 g of triethoxymethane and 50 ml of N,N-dimethylformamide and heated under nitrogen and a solution of 16.9 g of methyl anthranilate in 15 ml of N,N-dimethylformamide was added to the hot mixture and stirred for 15 minutes. The mixture was then cooled to room temperature and stirred for 16 hours. The white crystals which formed were separated by filtration, washed first with N,N-dimethylformamide and then with 2-propanol, and vacuum oven dried to give N1 -(1H-tetrazol-5-yl)-N2 -(2-carbomethoxyphenyl)formamidine which was identical with authentic material.

Workup

  1. temperatureheated under nitrogen
  2. stirringstirred for 16 hours
  3. customThe white crystals which formed
  4. customwere separated by filtration
  5. washwashed first with N,N-dimethylformamide
  6. dry with materialwith 2-propanol, and vacuum oven dried

Sources & evidence

ORD record
ord-cb599598dc6749b0995f197958d3f6a4
Source dataset
uspto-grants-1987_02
Patent number
US04644065

Reaction notes

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