Hydrochloric Acid → HCID 87568755, compound

HRID 661344Notes

Reaction equation

HRID 661344 reaction equation
Cl.C([N:4]([C:10]1[N:15]=[C:14]([CH2:16][O:17]/[N:18]=[C:19](\[C:26]2[N:30]([CH3:31])[N:29]=[N:28][N:27]=2)/[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=[CH:12][CH:11]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=O.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[CH2:5]([NH:4][C:10]1[N:15]=[C:14]([CH2:16][O:17]/[N:18]=[C:19](\[C:26]2[N:30]([CH3:31])[N:29]=[N:28][N:27]=2)/[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=[CH:12][CH:11]=1)[CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 87568797HCID 87568797, compound

Product 1

HCID 87568755HCID 87568755, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.5 ml of 3 M hydrochloric acid were added to 5 ml of an ethyl acetate solution of the (Z)-(1-methyl-1H-tetrazol-5-yl) phenylmethanone-O-(6-(N-formyl-N-n-pentylamino)pyridin-2-ylmethyl) oxime obtained in Example 1 followed by stirring for 5 hours at room temperature. The pH of the reaction liquid was adjusted to pH 7 by adding aqueous sodium carbonate solution thereto. After extracting with ethyl acetate, the product was washed with water and dried with anhydrous magnesium sulfate followed by distilling off the solvent. The resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=2/1 (v/v)) to obtain 0.14 g of (Z)-(6-n-pentylaminopyridin-2-yl)methoxyimino-(1-methyl-1H-tetrazol-5-yl)phenylmethane (compound no. 1-6 in the previous tables).

Workup

  1. customThe pH of the reaction liquid
  2. extractionAfter extracting with ethyl acetate
  3. washthe product was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationby distilling off the solvent
  6. customThe resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=2/1 (v/v))

Sources & evidence

ORD record
ord-91db8a5610ff45a09247cd71403240cd
Source dataset
uspto-grants-2011_12
Patent number
US08084613B2

Reaction notes

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