Sodium Acetate → HCID 178502649, compound

HRID 30439Notes

Reaction equation

HRID 30439 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[NH:19])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[O:29]([NH2:31])[CH3:30].C([O-])(=O)C.[Na+]>CO.C([O-])(O)=O.[Na+]>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:18](=[NH:19])[CH:17]=[CH:16][C:13]2[CH:12]=[CH:11][C:10]([C:7]3[CH:8]=[CH:9][C:4]([C:1](=[N:31][O:29][CH3:30])[CH3:2])=[CH:5][CH:6]=3)=[CH:15][CH:14]=2)=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 178466078HCID 178466078, compound

Product 1

HCID 178502649HCID 178502649, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 0.04 g (0.11 mmol) of 3-(4′-acetyl-biphenyl-4-yl)-N-(4-chloro-phenyl) -acrylamidine, 0.028 g (0.33 mmol) of methoxylamine hydrochloride and 0.027 g (0.33 mmol) of sodium acetate in 3 mL of methanol was heated under microwave (100 W, 5 min). Diluted with 20 mL of NaHCO3, it was extracted with two 10 mL portions of ethyl acetate. The combined organic extracts were washed with 10 mL of brine, dried over Na2SO4, filtered and concentrated. The residue was purified by preparative TLC eluting with 70% ethyl acetate in hexanes plus 1% NH4OH to give 0.004 g of N-(4-chloro-phenyl)-3-[4′-(1-methoxyimino-ethyl)-biphenyl-4-yl]-acrylamidine.

Workup

  1. temperaturewas heated under microwave (100 W, 5 min)
  2. extractionwas extracted with two 10 mL portions of ethyl acetate
  3. washThe combined organic extracts were washed with 10 mL of brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative TLC
  8. washeluting with 70% ethyl acetate in hexanes plus 1% NH4OH

Sources & evidence

ORD record
ord-6f5afaaf9cd544bbaaf3d08256ec9705
Source dataset
uspto-grants-2008_09
Patent number
US07423149B2

Reaction notes

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