Dimethyl Sulfoxide → HCID 57785864, compound

HRID 1399060Notes

Reaction equation

HRID 1399060 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[C:22]([F:25])([F:24])[F:23])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH2:26][OH:27])=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(C)=O>ClCCl.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:26]=[O:27])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[C:22]([F:24])([F:23])[F:25])[CH2:12][CH2:13][CH2:14][N:7]21

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 57785948HCID 57785948, compound

Product 1

HCID 57785864HCID 57785864, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Sulfur trioxide-pyridine complex (23.4 g, 147 mmol) was added to a stirred solution of {9-chloro-1-[4-chloro-2-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl}methanol (8.72 g, 20.9 mmol), triethylamine (23.3 mL), and dimethyl sulfoxide (140 mL) in dichloromethane (30 mL) at room temperature, and the mixture was stirred at room temperature for 3 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with diisopropyl ether to give the title compound as a colorless powder (6.90 g, 16.7 mmol, 80%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-ad8ca186ba4b41d0b3c95d698a8017f6
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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