Oxalyl chloride → HCID 53690444, compound

HRID 1741146Notes

Reaction equation

HRID 1741146 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=[CH2:15])C(O)=O.C(Cl)(=O)[C:17](Cl)=[O:18].[C:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:25])[NH:23][NH2:24]>O1CCCC1.CN(C)C=O>[C:27]([O:26][C:22]([N:23]([C:17](=[O:18])[CH:15]=[CH:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[NH2:24])=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 70091tert-Butyl carbazateHCID 21867142HCID 21867142, compound

Product 1

HCID 53690444HCID 53690444, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred solution of 2-naphthyl acrylic acid (5.0 g, 25.0 mmol) in dry tetrahydrofuran (100 ml) and N,N-dimethylformamide (0.2 ml) was added dropwise at 0° C. oxalyl chloride (4.8 g, 38.0 mmol). The mixture was stirred for 1 h at room temperature and the solvent was evaporated in vacuo affording crude acid chloride. To a solution of tert-butyl carbazate (6.7 g, 50.0 mmol) in dry tetrahydrofuran (80 ml) was added dropwise a solution of the acid chloride in dry tetrahydrofuran (50 ml) at 0° C. The resulting reaction mixture was stirred for 17 h at room temperature and the solvent was evaporated in vacuo. To the residue was added water (200 ml) and ethyl acetate (200 ml) and the phases were separated. The organic phase was washed with 0.1 N sodium hydroxide (2×100 ml), dried (MgSO4), filtered and evaporated in vacuo. The solid residue was suspended in heptane (50 ml), filtered off and dried in vacuo at 50° C. which afforded 4.7 g (59%) of N-(3-naphthalen-2-yl-acryloyl)hydrazine carboxylic acid tert butyl ester as a solid.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customaffording crude acid chloride
  3. customThe resulting reaction mixture
  4. stirringwas stirred for 17 h at room temperature
  5. customthe solvent was evaporated in vacuo
  6. additionTo the residue was added water (200 ml) and ethyl acetate (200 ml)
  7. customthe phases were separated
  8. washThe organic phase was washed with 0.1 N sodium hydroxide (2×100 ml)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. filtrationfiltered off
  13. customdried in vacuo at 50° C. which

Sources & evidence

ORD record
ord-32a628a2b31e4d299af11b7038431717
Source dataset
uspto-grants-1999_10
Patent number
US05972978

Reaction notes

Loading…