Dimethyl Sulfoxide → HCID 59334473, compound

HRID 1639741Notes

Reaction equation

HRID 1639741 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1[N:22]=[C:15]2[C:16]([CH2:20][OH:21])=[CH:17][CH:18]=[CH:19][N:14]2[N:13]=1.C(N(CC)CC)C>ClCCl>[CH3:11][C:12]1[N:22]=[C:15]2[C:16]([CH:20]=[O:21])=[CH:17][CH:18]=[CH:19][N:14]2[N:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59334623HCID 59334623, compound

Product 1

HCID 59334473HCID 59334473, compoundYield 83,613.297%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen atmosphere, to a solution of oxalyl chloride (16.0 mL, 180 mmol) in dichloromethane (200 mL) was added dimethyl sulfoxide (30.0 mL, 0.420 mol) 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-8-yl)methanol (23.0 g, 0.141 mmol) in dichloromethane (82 mL), and the mixture was stirred for 2 hr. To the reaction mixture was added triethylamine (99.0 mL, 0.710 mol) at −78° C., and the mixture was stirred for 1 hr and warmed to room temperature. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (methanol/ethyl acetate=1/10) to give the title compound (19.0 g, yield 84%).

Workup

  1. stirringthe mixture was stirred for 2 hr
  2. stirringthe mixture was stirred for 1 hr
  3. concentrationAfter concentration under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=1/10)

Sources & evidence

ORD record
ord-206ee832da734f589bc198df39e57e5d
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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