Stannous Chloride → HCID 22642382, compound

HRID 1773012Notes

Reaction equation

HRID 1773012 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:15])[C:12]([CH3:14])=[CH2:13])=[CH:6][CH:5]=1)([O-])=O.[Sn](Cl)Cl>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:15])[C:12]([CH3:14])=[CH2:13])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 133964192-Methyl-N-(4-nitrophenyl)prop-2-enamide

Product 1

HCID 22642382HCID 22642382, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Into a reaction vessel fitted with a cooling pipe, a stirrer, a thermometer and a nitrogen feed pipe, 20 parts of the N-(4-nitrophenyl)methacrylamide and 315 parts of ethanol were fed, which were dissolved therein, and thereafter the solution formed was cooled to 0° C. While the reaction solution obtained was kept at 0° C., 65 parts of tin(II) chloride was dividedly added thereto. After its addition was completed, the reaction solution was heated to room temperature, and, as it was, the reaction was carried out for 20 hours. After the reaction was completed, the solvent was evaporated off under reduced pressure, then 200 parts of ion-exchanged water was added to the reaction solution, and its pH was adjusted to 7 with use of an aqueous 12 mol/liter sodium hydroxide solution. To the solid having come precipitated, 200 parts of ethyl acetate was added, and insoluble matter was separated by filtration. The filtrate obtained was washed with 200 parts of ion-exchanged water, which was then dried with sodium sulfate, and thereafter the solvent was evaporated off under reduced pressure. The residue obtained was purified by silica gel column chromatography to obtain 12 parts of an intermediate N-(4-aminophenyl)methacrylamide (yield: 71%).

Workup

  1. customInto a reaction vessel fitted with a cooling pipe, a stirrer
  2. dissolutionwhich were dissolved
  3. customthe solution formed
  4. customWhile the reaction solution obtained
  5. customwas kept at 0° C.
  6. additionAfter its addition
  7. temperaturethe reaction solution was heated to room temperature
  8. customthe solvent was evaporated off under reduced pressure
  9. addition200 parts of ion-exchanged water was added to the reaction solution, and its pH
  10. customTo the solid having come precipitated
  11. addition200 parts of ethyl acetate was added
  12. custominsoluble matter was separated by filtration
  13. customThe filtrate obtained
  14. washwas washed with 200 parts of ion-exchanged water, which
  15. dry with materialwas then dried with sodium sulfate
  16. customthe solvent was evaporated off under reduced pressure
  17. customThe residue obtained
  18. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-caf59e152a4b433e8c62971d736161cf
Source dataset
uspto-grants-2016_02
Patent number
US09250552B2

Reaction notes

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