Acetic Anhydride → HCID 178476706, compound

HRID 2169232Notes

Reaction equation

HRID 2169232 reaction equation
CC([O:4][C:5]([CH3:7])=[O:6])=O.O[NH:9][C:10](=[NH:24])[CH2:11][C:12]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][CH:15]=[CH:14][N:13]=1.C(OCC)(=O)C>O>[C:5]([O:4][NH:24][C:10](=[NH:9])[CH2:11][C:12]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][CH:15]=[CH:14][N:13]=1)(=[O:6])[CH3:7]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 178510888HCID 178510888, compound

Product 1

HCID 178476706HCID 178476706, compoundYield 42.94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ac2O (30 mL) was added to N-hydroxy-2-(3-phenyl-pyridin-2-yl)-acetamidine (160) (5.3 g, 23.35 mmol) at room temperature. A purple colored solution was formed, after a few hours a dark brown solution was formed which was stirred for 6 h at room temperature. Silica thin layer chromatography was performed (100% ethyl acetate, Rf=0.6). Cold water was added, the mixture was extracted with ethyl acetate (3×50 mL), the organic part was dried and concentrated, the crude product was purified by a CombiFlash column (eluted at 50% ethyl acetate in hexane) to get 2-(3-phenylpyridin-2-yl)ethanimidamido acetate (161) (2.7 g, 42.94% pure and 2 g mixture) as a yellow solid.

Workup

  1. customA purple colored solution was formed, after a few hours a dark brown solution
  2. customwas formed which
  3. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  4. customthe organic part was dried
  5. concentrationconcentrated
  6. customthe crude product was purified by a CombiFlash column (eluted at 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-47f0a1ede5084cf9ae40d49f6c1fa2c5
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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