2-Cyanoacetyl chloride → HCID 69607367, compound

HRID 1244159Notes

Reaction equation

HRID 1244159 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][S:8][C:7]=1[NH2:19])=[O:5])[CH3:2].[C:20]([CH2:22][C:23](Cl)=[O:24])#[N:21]>C(Cl)Cl.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][S:8][C:7]=1[NH:19][C:23](=[O:24])[CH2:22][C:20]#[N:21])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 110515942-Cyanoacetyl chloride2×HCID 69607355HCID 69607355, compound

Product 1

HCID 69607367HCID 69607367, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-4-styryl-thiophene-3-carboxylic acid ethyl ester (0.1298 g, 0.475 mmol) S was dissolved in anhydrous CH2Cl2 (2.0 mL). This was treated with cyanoacetyl chloride (0.713 mL, 0.713 mmol, 1 M in CH2Cl2) and stirred at room temperature for 1 hr. More cyanoacetyl chloride (0.238 mL, 0.238 mmol) was added and stirring was continued at room temperature for 1 hr then refluxed for 30 min. The reaction was diluted with EtOAc (25 mL). This was washed with sat. NaHCO3 (1×25 mL), H2O (1×25 mL), and brine (1×25 mL). The organic layer was dried (Na2SO4), filtered and the solvent removed in vacuo to give 0.0803 g (50%) of crude 7 which was carried on to the next step.

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for 1 hr
  3. temperaturethen refluxed for 30 min
  4. washThis was washed with sat. NaHCO3 (1×25 mL), H2O (1×25 mL), and brine (1×25 mL)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customto give 0.0803 g (50%) of crude 7 which

Sources & evidence

ORD record
ord-7f77a490a7fc4ac2906a5a0bfacaa1f1
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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