Dimethyl Sulfoxide → HCID 59334616, compound

HRID 1639827Notes

Reaction equation

HRID 1639827 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][C:12]1[N:22]=[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([CH2:20][OH:21])[N:14]2[N:13]=1.C(N(CC)CC)C>ClCCl>[CH3:11][C:12]1[N:22]=[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([CH:20]=[O:21])[N:14]2[N:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59334513HCID 59334513, compound

Product 1

HCID 59334616HCID 59334616, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of dimethyl sulfoxide (7.83 mL, 110 mmol) in dichloromethane (100 mL) was added oxalyl chloride (4.83 mL, 55.2 mmol) at −78° C., and the mixture was stirred for 30 min. To the reaction mixture was added a solution of (2-methyl[1,2,4]triazolo[1,5-a]pyridin-5-yl)methanol (3.00 g, 18.4 mmol) in dichloromethane (84.0 mL), and the mixture was stirred for 2 hr. To the reaction mixture was added triethylamine (22.3 mL, 165 mmol) at −78° C., and the mixture was stirred for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/3) to give the title compound (2.80 g, yield 95%).

Workup

  1. stirringthe mixture was stirred for 2 hr
  2. stirringthe mixture was stirred for 1 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-d29e65bacb8f47c0ad8c5b82a6d6d5e2
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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