Hydrochloric Acid → HCID 178489886, compound

HRID 746092Notes

Reaction equation

HRID 746092 reaction equation
C([C:3]1[N:4]=[C:5]([CH2:8][C:9]2C=CC(OC)=[CH:11][CH:10]=2)[NH:6][CH:7]=1)#N.[CH3:17][Mg]Cl.Cl.[C:21]([O-:24])([O-])=O.[Na+].[Na+].[CH2:27]1[CH2:31][O:30][CH2:29][CH2:28]1>>[C:21]([C:3]1[N:4]=[C:5]([CH2:8][C:9]2[CH:28]=[CH:27][C:31]([O:30][CH3:29])=[CH:11][CH:10]=2)[NH:6][CH:7]=1)(=[O:24])[CH3:17]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 10340Sodium CarbonateHCID 178418332HCID 178418332, compoundHCID 178489888HCID 178489888, compound

Product 1

HCID 178489886HCID 178489886, compoundYield 100%

Procedure

To a solution of XXV (2.11 g, 0.01 mol) in THF (50 mL) was added with stirring at room temperature methyl magnesium chloride (12 mL, 2.8M, 0.034 mol) in THF. After 24 hours, 3N HCl (50 mL) was added dropwise with stirring and the resulting mixture heated at reflux for 20 minutes. After cooling to room temperature, the solution was neutralized with solid Na2CO3 and extracted with CHCl3 (3X). The organic extracts were dried, filtered and concentrated to dryness to yield 2.35 g (100%) of XXVI; m.p. 147°-48° C. (CH3CN).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 20 minutes
  3. extractionextracted with CHCl3 (3X)
  4. customThe organic extracts were dried
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-87d9a8f0ecf34aabaa006b0e7dbb012d
Source dataset
uspto-grants-1986_07
Patent number
US04602093

Reaction notes

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