Ethanol → HCID 89482802, compound

HRID 1772187Notes

Reaction equation

HRID 1772187 reaction equation
[C:1]([CH2:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][NH:7]1)=O)#[N:2].[CH:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].C(O)C.[CH3:25][NH:26][NH2:27]>C(OCC)(=O)C>[CH3:25][N:26]1[C:1]([NH2:2])=[CH:3][C:4]([CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][NH:7]2)=[N:27]1.[CH:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

5

Reactant 3

HCID 702EthanolHCID 6061MethylhydrazineHCID 89483016HCID 89483016, compound

Product 1

HCID 89482802HCID 89482802, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under nitrogen atmosphere, to a 250 mL three-neck reaction flask were added the compound of Example 11A (16.0 g, 55.9 mmol), ethanol (80 mL) and methylhydrazine (12 mL, 224 mmol). The mixture was refluxed for 5 hr. The reaction was stopped. Ethanol was removed by rotary-evaporation to obtain a crude product. The crude product was subject to column chromatography (eluant: petroleum ether:ethyl acetate=1:1) to give 11.7 g of the title compound. Yield: 66.6%. MS (ESI): m/z 315 (M+H)+

Workup

  1. temperatureThe mixture was refluxed for 5 hr
  2. customEthanol was removed by rotary-evaporation
  3. customto obtain a crude product

Sources & evidence

ORD record
ord-e44175866db44007824a4945ffcb537c
Source dataset
uspto-grants-2016_02
Patent number
US09249172B2

Reaction notes

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