Dichloromethane → HCID 14501796, compound

HRID 893528Notes

Reaction equation

HRID 893528 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]2SCCCS2)=[CH:6][C:5]([N:14]2[C:18](=[O:19])[N:17]([CH:20]([F:22])[F:21])[C:16]([CH3:23])=[N:15]2)=[C:4]([F:24])[CH:3]=1.BrN1C(=[O:31])CCC1=O.S(=O)(O)[O-].[Na+].C(Cl)Cl>CC(C)=O.C(#N)C.O.CCCCCCC>[Cl:1][C:2]1[C:7]([CH:8]=[O:31])=[CH:6][C:5]([N:14]2[C:18](=[O:19])[N:17]([CH:20]([F:22])[F:21])[C:16]([CH3:23])=[N:15]2)=[C:4]([F:24])[CH:3]=1

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 15764668HCID 15764668, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 14501796HCID 14501796, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent2×HCID 8900HeptaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2.0 g (0.0051 mole) of 1-[4-chloro-2-fluoro-5-(1,3-dithian-2-yl)phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one in 25 mL of acetone and 25 mL of acetonitrile is added slowly to a stirred, cold (0° C.) solution of 5.5 g (0.031 mole) of N-bromosuccinimide in 80 mL of acetonitrile and 20 mL of water. The reaction mixture is stirred at 0° C. for about one hour. Approximately 15 mL of an aqueous, saturated sodium bisulfite solution is added. A mixture of 25 mL of methylene chloride and 25 mL of n-heptane is added, and the mixture is shaken in a separatory funnel. The organic phase is removed and is washed in succession with an aqueous, saturated sodium bicarbonate solution, water, and an aqueous, saturated sodium chloride solution. The washed organic phase is dried over anhydrous magnesium sulfate and is filtered. The filtrate is evaporated under reduced pressure to leave a residue. This residue is purified by column chromatography on silica gel to yield 1-(4-chloro-2-fluoro-5-formylphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one.

Workup

  1. additionis added
  2. stirringthe mixture is shaken in a separatory funnel
  3. customThe organic phase is removed
  4. washis washed in succession with an aqueous, saturated sodium bicarbonate solution, water
  5. dry with materialThe washed organic phase is dried over anhydrous magnesium sulfate
  6. filtrationis filtered
  7. customThe filtrate is evaporated under reduced pressure
  8. customto leave a residue
  9. customThis residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f52828e2db4946b5a2d94c39e9525366
Source dataset
uspto-grants-1992_06
Patent number
US05125958

Reaction notes

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