Dimethyl Sulfoxide → HCID 21472504, compound

HRID 2256278Notes

Reaction equation

HRID 2256278 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]([CH2:31][CH2:32][OH:33])[CH2:20][C:21]([N:23]([CH3:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:22])[CH:15]=[CH:16][C:17]=1[Cl:18].CCN(CC)CC>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]([CH2:31][CH:32]=[O:33])[CH2:20][C:21]([N:23]([CH3:30])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:22])[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19029318HCID 19029318, compound

Product 1

HCID 21472504HCID 21472504, compoundYield 117.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

Oxalyl chloride (7.74 g) in CH2Cl2 (80 mL) was added to a -78° C. solution of DMSO (9.5 g) in CH2Cl2 (30 mL) over 15 mins. This mixture was stirred for 15 minutes whereupon a CH2Cl2 (50 mL) solution of 3,4-Dichloro-beta-(2-hydroxyethyl)-N-methyl-N-phenylbenzenepropanamide (17.15 g) was added over 20 minutes. The mixture was stirred for 30 minutes and then treated with a solution of Et3N (14.76 g) in CH2Cl2 (20 mL) and stirred for an additional 30 minutes at -78° C., followed by 1.5 hours at room 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 (20 g). Silica gel chromatography eluting with 5-15% EtOAc/Hex gave the title compound (15.2 g).

Workup

  1. additionwas added over 20 minutes
  2. stirringstirred for an additional 30 minutes at -78° C.
  3. waitfollowed by 1.5 hours at room temperature
  4. washThe reaction mixture was washed with water (100 mL)
  5. customthe organic fraction separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1b904705649143ad999c97938aa02309
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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