Acetic Acid → HCID 22597401, compound

HRID 1760218Notes

Reaction equation

HRID 1760218 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH2:10][C:11]#[N:12])[C:3]=1[N+:13]([O-])=O.O.C(O)(=O)C>C(O)C.[Zn]>[NH2:13][C:3]1[C:4]([NH:8][CH2:9][CH2:10][C:11]#[N:12])=[N:5][CH:6]=[N:7][C:2]=1[Cl:1]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 22597439HCID 22597439, compound

Product 1

HCID 22597401HCID 22597401, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

2-[(6-Chloro-5-nitro-4-pyrimidinyl)amino]ethyl cyanide (18.7 g, 82.2 mmol) was dissolved in 180 ml ethanol, 180 ml water and 18 ml acetic acid, and zinc powder was added slowly thereto at 0° C. The reaction solution was returned to room temperature and stirred for 30 minutes. Then, the insoluble matters were filtered off, and the filtrate was evaporated. The residue was diluted with ethyl acetate and washed with water and brine, and the organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was suspended in diethyl ether, and the precipitated solid was collected by filtration to give the title compound which was then washed with diethyl ether to give the title compound (44.6 g, 51%).

Workup

  1. customat 0° C
  2. customwas returned to room temperature
  3. filtrationThen, the insoluble matters were filtered off
  4. customthe filtrate was evaporated
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-c71f4386a1d64b359aee6bcfe0acf481
Source dataset
uspto-grants-2005_01
Patent number
US06841549B1

Reaction notes

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