Dimethyl Sulfoxide → HCID 56644431, compound

HRID 2040881Notes

Reaction equation

HRID 2040881 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[C:14]([C:18]#[C:19][C:20]2[CH2:24][C:23]3([C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]([OH:33])[CH2:25]3)[O:22][N:21]=2)[CH:15]=[CH:16][CH:17]=1>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[C:14]([C:18]#[C:19][C:20]2[CH2:24][C:23]3([C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:26](=[O:33])[CH2:25]3)[O:22][N:21]=2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 56644643HCID 56644643, compound

Product 1

HCID 56644431HCID 56644431, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of oxalyl chloride (64.6 μL, 0.74 mmol) in 5 mL of anhydrous CH2Cl2 was cooled to −60° C.; DMSO (105 μL, 1.48 mmol) was added dropwise so as to keep the reaction at the same temperature. After 15 min. the compound of Example 82 (174 mg, 0.49 mmol) dissolved in 1 mL of anhydrous CH2Cl2 was added and after 30 minutes TEA (0.413 mL, 2.96 mL) was added dropwise. Turning off the cooling and heating up to r.t., the reaction mixture was stirred for 3 hours, then it was quenched with H2O, extracted with CH2Cl2 and dried on Na2SO4. The residue from evaporation was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Petroleum Ether-EtOAc from 95:5 to 1:1) to give the title compound as a brownish oil. Yield: 50%

Workup

  1. customthe reaction at the same temperature
  2. additionwas added dropwise
  3. customit was quenched with H2O
  4. extractionextracted with CH2Cl2
  5. customdried on Na2SO4
  6. customThe residue from evaporation
  7. customwas purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Petroleum Ether-EtOAc from 95:5 to 1:1)

Sources & evidence

ORD record
ord-859f120076904732a7326d4dda2a2366
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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