Sodium Bicarbonate → HCID 22236886, compound

HRID 1743976Notes

Reaction equation

HRID 1743976 reaction equation
[N:1]([CH2:4][C:5]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)([CH2:8][CH2:9][O:10]C1CCCCO1)[C:6]#[N:7])=[N+:2]=[N-:3].C(=O)([O-])O.[Na+]>CO.Cl>[N:1]([CH2:4][C:5]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)([CH2:8][CH2:9][OH:10])[C:6]#[N:7])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22236947HCID 22236947, compound

Product 1

HCID 22236886HCID 22236886, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 4.72 g of the compound obtained in Step 3 in 100 ml of methanol was added 40 ml of IN HCl solution, and the resulting mixture was stirred for 6 hours. After the reaction was completed, the reaction solution was neutralized with sodium hydrogen carbonate solution, distilled under reduced pressure to remove methanol therefrom, and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue thus obtained was purified by a silica gel column chromatography using a mixture of ethyl acetate and n-hexane of 1:2 to obtain 3.24 g of the title compound as an oil.

Workup

  1. distillationdistilled under reduced pressure
  2. customto remove methanol
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue thus obtained
  7. customwas purified by a silica gel column chromatography
  8. additiona mixture of ethyl acetate and n-hexane of 1:2

Sources & evidence

ORD record
ord-9e422cc41c364f0cab3fa73a66496721
Source dataset
uspto-grants-2006_03
Patent number
US07012144B2

Reaction notes

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