Dimethyl Sulfoxide → HCID 18009118, compound

HRID 987497Notes

Reaction equation

HRID 987497 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]([N:24]2[CH:28]=[CH:27][N:26]=[C:25]2[CH3:29])[CH2:20][CH2:21][CH2:22][OH:23])=[CH:15][C:14]=1[F:30])#[N:12].C(N(CC)CC)C>ClCCl.CCOC(C)=O.CCCCCC>[C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]([N:24]2[CH:28]=[CH:27][N:26]=[C:25]2[CH3:29])[CH2:20][CH2:21][CH:22]=[O:23])=[CH:15][C:14]=1[F:30])#[N:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18009116HCID 18009116, compound

Product 1

HCID 18009118HCID 18009118, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of oxalyl chloride (0.114 mL, 1.305 mmol) in 3.0 mL of dichloromethane at −78° C. was added DMSO (0.185 mL, 2.60 mmol) dropwise. After 10 minutes, a solution of the alcohol from Step K (238 mg, 0.870 mmol) in 2 mL of dichloromethane was added dropwise, followed by triethylamine (0.424 mL, 3.04 mmol). The reaction was allowed to warm to room temperature over 30 minutes. The solution was poured into 80% EtOAc/hexane, washed with sat. aq. NaHCO3, water and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the titled compound as a yellow oil which was used without further purification in the next reaction.

Workup

  1. washwashed with sat. aq. NaHCO3, water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e804621f8aa54cc8b31f49baf72d372c
Source dataset
uspto-grants-2003_10
Patent number
US06632818B2

Reaction notes

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