Dimethyl Sulfoxide → HCID 59424218, compound

HRID 500532Notes

Reaction equation

HRID 500532 reaction equation
C(Cl)(=O)C([Cl:4])=O.CS(C)=O.[C:11]1(C)[CH:16]=[CH:15][CH:14]=[C:13]([N:17]2[N:21]=[N:20][C:19]([CH2:22][OH:23])=[N:18]2)[CH:12]=1.CCN(CC)CC>C(Cl)Cl.O>[Cl:4][C:11]1[CH:12]=[C:13]([N:17]2[N:21]=[N:20][C:19]([CH:22]=[O:23])=[N:18]2)[CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59424221(2-m-tolyl-2H-tetrazol-5-yl)-methanol

Product 1

HCID 59424218HCID 59424218, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of oxalyl chloride (4.0 mL, 46 mmol) in CH2Cl2 (100 mL) at −78° C. was added DMSO (6.5 mL, 92 mmol) dropwise. The mixture was stirred for 10 minutes after which the title compound from Example 13.2 (7.92 mg, 41.6 mmol) in CH2Cl2 (30 mL) was added dropwise. The mixture was stirred for an additional 30 minutes and Et3N (2.9 mL, 208 mmol) was added dropwise. The reaction was then allowed to warm to room temperature. Water (150 mL) was then added and the organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (10-20% EtOAc/hexanes) to yield the title compound as an orange oil (4.98 g, 64%).

Workup

  1. additionwas added dropwise
  2. washthe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (10-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-55f399fe3f5e4615ab7405b68af59cba
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

Loading…