Salicylic Acid → HCID 178484367, compound

HRID 2092640Notes

Reaction equation

HRID 2092640 reaction equation
[CH3:1][N:2]([CH3:9])[C:3]([NH:5][C:6](=[NH:8])[NH2:7])=[NH:4].[C:10]([OH:19])(=[O:18])[C:11]1[C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:13]>C(#N)C>[C:10]([O-:19])(=[O:18])[C:11]1[C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:13].[NH2:8][C:6]([NH:5][C:3]([N:2]([CH3:9])[CH3:1])=[NH2+:4])=[NH:7]

Participants

4

Reactant 2

HCID 338Salicylic AcidHCID 178484382HCID 178484382, compound

Product 1

HCID 178484367HCID 178484367, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

N,N-Dimethylimidodicarbonimidic diamide (metformin free base) (1.66 g, 12.8 mmol) was dissolved in acetonitrile (45 mL) and the resulting solution was filtered through a medium frit to remove a small amount of sodium chloride that precipitated. To the filtrate was added dropwise at room temperature (over a 2 minute period) a solution of salicylic acid (1.42 g, 10.3 mmol) in acetonitrile (20 mL). The reaction solution became warm and a white solid precipitated about 1 minute after the addition was complete. After stirring for 1 h at room temperature, the mixture was chilled to 0° C. for 1 h. The white solid was filtered and the solid was washed with 20 mL ice-cold acetonitrile. The material was dried for 5 minutes on the frit followed by transfer of the solid to a round-bottom flask and the material was left under high vacuum overnight to yield 2.27 g (82%) of the title compound as a crystalline white solid. MP 152-154° C.; 1H NMR (400 MHz, MeOD) 7.82 (dd, J=7.67, 1.66 Hz, 1 H), 7.26 (m, 1 H), 6.76 (m, 2 H), 3.03 (s, 6 H); 13C NMR (101 MHz, MeOD) 176.31, 162.72, 161.33, 160.57, 133.87, 131.77, 120.38, 119.10, 117.25, 38.09; MS (ESI−) for C7H6O3 m/z 137.1 (M-H)−.

Workup

  1. filtrationthe resulting solution was filtered through a medium frit
  2. customto remove a small amount of sodium chloride
  3. customthat precipitated
  4. temperatureThe reaction solution became warm
  5. customa white solid precipitated about 1 minute
  6. additionafter the addition
  7. temperaturethe mixture was chilled to 0° C. for 1 h
  8. filtrationThe white solid was filtered
  9. washthe solid was washed with 20 mL ice-cold acetonitrile
  10. customThe material was dried for 5 minutes on the frit
  11. customfollowed by transfer of the solid to a round-bottom flask
  12. waitthe material was left under high vacuum overnight

Sources & evidence

ORD record
ord-97ab0a8beda647b9a0c6e1b563b7c3e2
Source dataset
uspto-grants-2013_05
Patent number
US08440723B2

Reaction notes

Loading…