Acetohydrazide → HCID 57650585, compound

HRID 2063476Notes

Reaction equation

HRID 2063476 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]([C@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=S)[CH3:9])=[CH:4][CH:3]=1.[C:25]([NH:28][NH2:29])(=O)[CH3:26]>C(#N)C.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[C:25]([CH3:26])=[N:28][N:29]=[C:11]2[C@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14039AcetohydrazideHCID 57650584HCID 57650584, compound

Product 1

HCID 57650585HCID 57650585, compound

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a mixture of the product of Step B (1.7 g, 4.6 mmol) and acetic hydrazide (0.76 g, 9.2 mmol) in 30 ml acetonitile was added mercury (II) acetate (2.2 g, 6.9 mmol) and the mixture was stirred at room temperature for overnight. The mixture was filtered over a Celite-fritted funnel and washed with more acetonitrile. The filtrate was concentrated in vacuo. Run wash column yield the desired product containing minor impurities (1.3 g, 72%), was used in the next step without further purification.

Workup

  1. filtrationThe mixture was filtered over a Celite-fritted funnel
  2. washwashed with more acetonitrile
  3. concentrationThe filtrate was concentrated in vacuo
  4. washRun wash column

Sources & evidence

ORD record
ord-c239f37011df4052a4fc9114b05adc20
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

Loading…