Diketene → HCID 178468066, compound

HRID 227705Notes

Reaction equation

HRID 227705 reaction equation
[Cl: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>C(#N)C>[Cl: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 178507360HCID 178507360, compound

Product 1

HCID 178468066HCID 178468066, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
50 °C

Procedure

The product of Step (b) (0.4 g, 2.4 mmol) was dissolved in acetonitrile (1 ml). In a separate flask, diketene (0.18 ml, 2.4 mmol, stabilized with copper sulfate) was dissolved in acetonitrile (1 ml). The diketene solution was added to the amine suspension in three portions, the reaction mixture was sealed and heated to 50° C. for 18 hours. The solvent was evaporated to dryness and purified by silica gel chromatography eluting with 5% MeOH In CH2Cl2 to afford the title compound, (0.5 g, 83%); MS (ES+) m/e 252 [M+H]+.

Workup

  1. customthe reaction mixture was sealed
  2. customThe solvent was evaporated to dryness
  3. custompurified by silica gel chromatography
  4. washeluting with 5% MeOH In CH2Cl2

Sources & evidence

ORD record
ord-4d494284ae4f4a49bffa4af85e3909ed
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

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