Dimethyl Sulfoxide → HCID 67269934, compound

HRID 1695559Notes

Reaction equation

HRID 1695559 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.FC(F)(F)C([O-])=O.[NH:18]1[CH2:22][CH2:21][N:20]=[C:19]1[C:23]1[C:35]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28](=[O:36])[C:27]=2[CH:26]=[CH:25][CH:24]=1>ClCCl.O.C(N(CC)CC)C>[NH:18]1[CH:22]=[CH:21][N:20]=[C:19]1[C:23]1[C:35]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28](=[O:36])[C:27]=2[CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 84468TrifluoroacetateHCID 68898599HCID 68898599, compound

Product 1

HCID 67269934HCID 67269934, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
-65 °C

Procedure

In a 100 mL three-necked flask under an argon atmosphere, cool to −65° C., a solution of 0.65 mL of oxalyl chloride in 5 mL of dichloromethane, then add, dropwise, 0.94 mL of dimethylsulphoxide on 3A molecular sieve. Stir for 10 minutes, then add, dropwise, a solution of 1.65 g of trifluoroacetate of 4-(4,5-dihydro-1H-imidazol-2-yl)-fluoren-9-one acid in 15 mL of dichloromethane then 5 mL of triethylamine. Stir at −65° C. for one hour, then leave to return to room temperature and stir for 2 hours. Pour the reaction mixture into water, and extract with dichloromethane. Wash the organic phases with a saturated aqueous solution of sodium chloride, dry over magnesium sulphate and evaporate to dryness at reduced pressure. After purification by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and methanol (98/2 by volume), we obtain 560 mg of 4-(1H-imidazol-2-yl)-fluoren-9-one in the form of a yellow powder to be used as it is in the next stage, and having the following characteristics:

Workup

  1. additionadd
  2. stirringStir at −65° C. for one hour
  3. customleave
  4. customto return to room temperature
  5. stirringstir for 2 hours
  6. extractionextract with dichloromethane
  7. washWash the organic phases with a saturated aqueous solution of sodium chloride
  8. dry with materialdry over magnesium sulphate
  9. customevaporate to dryness at reduced pressure
  10. customAfter purification by flash chromatography on silica gel (40-63 μm)
  11. washeluting with a mixture of dichloromethane and methanol (98/2 by volume), we

Sources & evidence

ORD record
ord-2c3c4c770bea452696292425d7a57a5a
Source dataset
uspto-grants-2012_04
Patent number
US08163750B2

Reaction notes

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