Diketene → HCID 178468064, compound

HRID 227722Notes

Reaction equation

HRID 227722 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[NH:4][N:3]=1.[CH2:12]=[C:13]1[O:17][C:15](=[O:16])[CH2:14]1>CC#N>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:15](=[O:16])[CH2:14][C:13](=[O:17])[CH3:12])[CH:9]=2)[NH:4][N:3]=1

Participants

4

Reactant 2

HCID 12661Diketene2×HCID 178507356HCID 178507356, compound

Product 1

HCID 178468064HCID 178468064, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
50 °C

Procedure

The product of Step (b) (4.00 g, 18.86 mmol, 1 equiv) was suspended In CH3CN (20 mL). In a separate flask, diketene (1.45 mL, 18.89 mmol, 1 equiv) was dissolved in CH3CN (10 mL) The diketene solution was added to the initial suspension, and the mixture was heated to 50° C. for 18 hours. The reaction mixture was cooled and concentrated en vacuo. The resulting residue was purified by flash chromatography to afford 1.47 g (26%) of the product as a pink solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated en vacuo
  3. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4174d3a74dc64a7c9ee1226d011a163d
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

Loading…