Dimethyl Sulfoxide → HCID 19029303, compound

HRID 2256324Notes

Reaction equation

HRID 2256324 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].CS(C)=O.[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]([CH2:34][CH2:35][OH:36])[CH2:20][C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28](OC)=[C:27](F)[CH:26]=2)=[O:22])[CH:15]=[CH:16][C:17]=1[Cl:18].[CH3:37]CN(CC)CC>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]([CH2:34][CH:35]=[O:36])[CH2:20][C:21]([N:23]([CH3:37])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:3][CH3:2])[CH:26]=2)=[O:22])[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19029306HCID 19029306, compound

Product 1

HCID 19029303HCID 19029303, compoundYield 130.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

Oxalyl chloride (1.44 g) in CH2Cl2 (100 mL) was cooled to a -78° C. and treated with a solution of DMSO (1.84 g) in CH2Cl2 (20 mL) over 15 mins. This mixture was stirred for 15 minutes whereupon a CH2Cl2 (30 mL) solution of 3,4-Dichloro-beta-(2-hydroxyethyl)-N-[(3-fluoro-4-methoxyphenyl)methyl]benzenepropanamide (3.9 g) was added dropwise. The mixture was stirred for 30 minutes and then treated with a solution of Et3N (2.85 g) in CH2Cl2 (20 mL) and stirred for an additional 30 minutes at -78° C., then allowed to warm to ambient temperature. The reaction mixture was washed with water (100 mL), the organic fraction separated, dried over MgSO4, filtered and concentrated under reduced pressure to yield an oil (5.0 g). Silica gel chromatography eluting with 10% EtOAc/CH2Cl2 gave the title compound (3.6 g).

Workup

  1. additionwas added dropwise
  2. stirringstirred for an additional 30 minutes at -78° C.
  3. washThe reaction mixture was washed with water (100 mL)
  4. customthe organic fraction separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-903c37432ebb43c79770eada93baf5d0
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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