Methanol → HCID 9843038, compound

HRID 2231098Notes

Reaction equation

HRID 2231098 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:13]([F:16])([F:15])[F:14])=[N:10][C:9]=2[C:17]2[CH:22]=[CH:21][C:20](SC)=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.O[O:26][S:27]([O-:29])=O.[K+].[CH3:31]O>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][C:11]([C:13]([F:14])([F:16])[F:15])=[N:10][C:9]=2[C:17]2[CH:18]=[CH:19][C:20]([S:27]([CH3:31])(=[O:29])=[O:26])=[CH:21][CH:22]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 54571700HCID 54571700, compound

Product 1

HCID 9843038HCID 9843038, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of imidazole from step 4 above (550 mg, 1.6 mmol) in methanol (10 ml) was stirred at 25° C. while a solution of OXONE® (1.6 g) in water (3 ml) was added. The reaction mixture was stirred for 3 hours at room temperature, poured into water (50 ml) and extracted with methylene chloride. After drying the organic layer (Na2SO4) and concentration, the residue was treated with cold ethyl acetate, filtered, and air dried to give 490 mg (80%) of the titled material which was identical with Examples 1 Method A and Method B.

Workup

  1. additionwas added
  2. extractionextracted with methylene chloride
  3. customAfter drying
  4. concentrationthe organic layer (Na2SO4) and concentration
  5. additionthe residue was treated with cold ethyl acetate
  6. filtrationfiltered
  7. customair dried

Sources & evidence

ORD record
ord-19502174b6d14a5dba0d5ea29f9ffea2
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

Loading…