NSC650981 → HCID 9943734, compound

HRID 852312Notes

Reaction equation

HRID 852312 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N+:12]([O-])=[CH:11][N:10]([CH3:14])[C:9]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.CC1(C)C(=[S:26])C(C)(C)C1=O>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11](=[S:26])[N:10]([CH3:14])[C:9]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 373949NSC650981HCID 58752326HCID 58752326, compound

Product 1

HCID 9943734HCID 9943734, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

0.5 g of 5-(4-fluorophenyl)-4-(4-pyridyl)-3-methylimidazole N-oxide from example 1d were dissolved in 20 ml of CHCl3, and the reaction mixture was cooled in an ice-bath. An equimolar solution of 2,2,4,4-tetramethyl-3-thionocyclobutanone in CHCl3 was slowly added dropwise to the initial charge, and the mixture was then stirred in the ice-bath for 30 min. The ice-bath was removed, and stirring was continued at room temperature for 1 h. The solvent was then removed using a rotary evaporator, and the solid residue was triturated in diethyl ether. The precipitate was filtered off and dried under reduced pressure. The yield was 98%.

Workup

  1. temperaturethe reaction mixture was cooled in an ice-bath
  2. additioninitial charge
  3. customThe ice-bath was removed
  4. customThe solvent was then removed
  5. customa rotary evaporator
  6. customthe solid residue was triturated in diethyl ether
  7. filtrationThe precipitate was filtered off
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-4b66c1eade374f1c82cd13167faea5c4
Source dataset
uspto-grants-2007_08
Patent number
US07253191B2

Reaction notes

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