Hydrochloric Acid → HCID 86756134, compound

HRID 1276060Notes

Reaction equation

HRID 1276060 reaction equation
N[C:2]1[C:3]([Cl:23])=[CH:4][C:5]([F:22])=[C:6]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]3[CH:19]=[CH:20][N:21]=[C:9]23)[CH:7]=1.[ClH:24].[C:25]([O:29][CH2:30][CH3:31])(=[O:28])[CH:26]=[CH2:27].N([O-])=O.[Na+]>O.[Cu]Cl.CC(C)=O>[Cl:23][C:3]1[C:2]([CH2:27][CH2:26][C:25]([O:29][CH:30]([Cl:24])[CH3:31])=[O:28])=[CH:7][C:6]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[N:10]3[CH:19]=[CH:20][N:21]=[C:9]23)=[C:5]([F:22])[CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 22114883HCID 22114883, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 86756134HCID 86756134, compound

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a mixture of 8-(5-amino-4-chloro-2-fluorophenyl)-7,8-dihydro-5-trifluoromethylimidazo[1,2-a]pyrimidin-7-one (1.5 g), copper(I) chloride (0.06 g) and acetone (30 ml) was added concentrated hydrochloric acid (1.13 g) and ethyl acrylate (5.0 g) under ice-cooled condition. Sodium nitrite (0.38 g) dissolved in water was added slowly under ice-cooled condition to the mixture, which was then stirred for 3 hours at room temperature. The reaction solution was poured into water and extracted with ethyl acetate. The extract layer was washed with diluted hydrochloric acid and water in this order, and dried on anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by a preparative thin-layer plate of silica gel (developing solvent: ethyl acetate/hexane=3/7) to give the compound of interest (0.5 g) as a pale yellow oil.

Workup

  1. temperaturecooled condition
  2. additionwas added slowly under ice-
  3. temperaturecooled condition to the mixture, which
  4. extractionextracted with ethyl acetate
  5. washThe extract layer was washed with diluted hydrochloric acid and water in this order
  6. dry with materialdried on anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by a preparative thin-layer plate of silica gel (developing solvent: ethyl acetate/hexane=3/7)
  9. customto give the compound of interest (0.5 g) as a pale yellow oil

Sources & evidence

ORD record
ord-72e315e6539f4476930913bf82f35fbd
Source dataset
uspto-grants-2000_12
Patent number
US06165942

Reaction notes

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