Chloroform → HCID 57236497, compound

HRID 2227196Notes

Reaction equation

HRID 2227196 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:25]=[CH:24][C:6]2[N:7]([C@@H:10]3[O:22][C@H:21]([CH3:23])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]3[O:12][C:13](=[O:15])[CH3:14])[CH:8]=[N:9][C:5]=2[CH:4]=1.[Br:28]N1C(=O)CCC1=O.C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>C1COCC1>[Br:28][C:8]1[N:7]([C@@H:10]2[O:22][C@H:21]([CH3:23])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]2[O:12][C:13](=[O:15])[CH3:14])[C:6]2[CH:24]=[CH:25][C:3]([C:2]([F:1])([F:26])[F:27])=[CH:4][C:5]=2[N:9]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 67184N-bromobutanimide2×HCID 516892Sodium BicarbonateHCID 54289108HCID 54289108, compound

Product 1

HCID 57236497HCID 57236497, compoundYield 115.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a refluxing solution of 0.2 g (0.52 mmol) of 5-Trifluoromethyl-1-(2,3-di-O-Acetyl-5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole in 10 mL of dry THF was added 0.2 g (1.1 mmol) of N-bromosuccinimide (NBS). The reaction mixture was further refluxed for 10 min. Additional 0.1 g of NBS was added. After 5 min, the mixture was poured into an ice-cooled solution of 20 mL CHCl3 and 20 mL sat. NaHCO3. The CHCl3 solution was separated and was further washed with sat. NaHCO3. After drying (MgSO4) and solvent removal, 0.28 g of the title compound was obtained as a semi-solid which was used without further purification in the following reaction.

Workup

  1. temperatureThe reaction mixture was further refluxed for 10 min
  2. customThe CHCl3 solution was separated
  3. washwas further washed with sat. NaHCO3
  4. customAfter drying
  5. custom(MgSO4) and solvent removal

Sources & evidence

ORD record
ord-9ebabf73cec045e98f84d32255481b30
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

Loading…