Bromoacetonitrile → HCID 136344267, compound

HRID 1669387Notes

Reaction equation

HRID 1669387 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[C:10](=[O:23])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]#[N:22])[CH:14]=1.[H-].[Na+].Br[CH2:27][C:28]#[N:29].CN(C)P(N(C)C)(N(C)C)=[O:33]>>[C:28]([CH2:27][O:33][N:5]1[C:6]([CH3:8])=[CH:7][C:2]([OH:1])=[C:3]([C:10](=[O:23])[CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]#[N:22])[CH:14]=2)[C:4]1=[O:9])#[N:29]

Participants

5

Reactant 4

HCID 11534BromoacetonitrileHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 136344268HCID 136344268, compound

Product 1

HCID 136344267HCID 136344267, compound

Procedure

To a solution of 0.50 g of 4-hydroxy-3-[3-[3-(cyanomethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone in 6 ml of hexamethylphosphoramide was added 46 mg of sodium hydride (60% oily) under ice-cooling, and this was stirred at room temperature for 1 hour. To the reaction mixture was added 0.33 ml of bromoacetonitrile under ice-cooling, and this was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure, and precipitated crystals were filtered, washed with t-butyl methyl ether, and dried to obtain 0.14 g of 1-(cyanomethoxy)-3-[3-[3-(cyanomethoxy)phenyl]-1-oxo-2-propenyl]-4-hydroxy-6-methyl-2(1H)-pyridinone [Compound No. (6c)] as a yellow crystal.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthis was stirred at room temperature for 2 hours
  4. distillationThe solvent was distilled off under reduced pressure
  5. customprecipitated crystals
  6. filtrationwere filtered
  7. washwashed with t-butyl methyl ether
  8. customdried

Sources & evidence

ORD record
ord-ed50559323e4424ea96914a1db2ecb84
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

Loading…