Dimethyl Sulfoxide → HCID 10176644, compound

HRID 1654764Notes

Reaction equation

HRID 1654764 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[N:11]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[OH:20])=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[C:21]1([C:19](=[O:20])[C:18]#[C:17][C:14]2[CH:13]=[CH:12][N:11]=[CH:16][CH:15]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 9990663HCID 9990663, compound

Product 1

HCID 10176644HCID 10176644, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Place oxalyl chloride (0.5 mL of a 2 M solution in methylene chloride, 1 mmol) under argon atmosphere and cool with a dry ice/acetone bath. Add dimethylsulfoxide (0.14 mL, 2 mmol) and stir for 10 minutes at -70° C. Add α-[(4pyridinyl)ethynyl]-benzenemethanol (0.18 g, 0.86 mmol) in methylene chloride (1 mL). Stir for 20 minutes at -78° C. Add triethylamine (0.56 mL, 4 mmol), remove the cooling bath and stir for 45 minutes. Pour onto silica gel and elute with 60% ethyl acetate/hexane. Evaporate the solvent in vacuo and recrystallize (hexane/chloroform) to yield 58.1 mg of the title compound; mp 74°-75° C.

Workup

  1. stirringstir for 45 minutes
  2. additionPour onto silica gel
  3. washelute with 60% ethyl acetate/hexane
  4. customEvaporate the solvent in vacuo
  5. customrecrystallize (hexane/chloroform)

Sources & evidence

ORD record
ord-6df61852509e4162b578367dc40244b0
Source dataset
uspto-grants-1995_04
Patent number
US05409942

Reaction notes

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