Sodium Azide → HCID 22114876, compound

HRID 1276044Notes

Reaction equation

HRID 1276044 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]=[C:9]2S(C)(=O)=O)=[CH:4][CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+]>C(#N)C.CCOCC.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]3[N:23]=[N:24][N:25]=[C:9]23)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 22114881HCID 22114881, compound

Product 1

HCID 22114876HCID 22114876, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3-(4-Chlorophenyl)-3,4-dihydro-2-methanesulfonyl-6-trifluoromethylpyrimidin-4-one (1.1 g) was dissolved in a mixture of acetonitrile (20 ml) with ether (20 ml) and was added with sodium azide (0.24 g) under ice-cooled condition. The thus obtained mixture was stirred for 30 minutes at room temperature and was added with saturated brine (50 ml). The mixture was extracted with ether and then dried on anhydrous magnesium sulfate followed by distilling off the solvent under reduced pressure. The residue was purified by a preparative thin-layer plate of silica gel (developing solvent: ethyl acetate/hexane=1.5/8.5) to give the compound of interest (0.7 g) as a white solid.

Workup

  1. temperaturecooled condition
  2. extractionThe mixture was extracted with ether
  3. dry with materialdried on anhydrous magnesium sulfate
  4. distillationby distilling off the solvent under reduced pressure
  5. customThe residue was purified by a preparative thin-layer plate of silica gel (developing solvent: ethyl acetate/hexane=1.5/8.5)
  6. customto give the compound of interest (0.7 g) as a white solid

Sources & evidence

ORD record
ord-72413764854e457893aaf9cab12a37c1
Source dataset
uspto-grants-2000_12
Patent number
US06165942

Reaction notes

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