Dichloromethane → HCID 54542963, compound

HRID 2256299Notes

Reaction equation

HRID 2256299 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:22][CH2:23]OS(C)(=O)=O)[CH2:10][C:11]([N:13]([CH3:21])[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[Li+].[Li+].[Br-:35].[Li+].C(Cl)Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:22][CH2:23][Br:35])[CH2:10][C:11]([N:13]([CH3:21])[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11125Lithium CarbonateHCID 82050Lithium BromideHCID 19029363HCID 19029363, compound

Product 1

HCID 54542963HCID 54542963, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Dichloro-beta-(2-methanesulfonyloxyethyl)-N-methyl-N-(4-chlorophenyl)benzene propanamide (6.3 g) in THF (50 mL) was treated with lithium carbonate (2.0 g) and lithium bromide (2.34 g). The mixture was heated at reflux temperature for 2 hours. The cooled reaction mixture was diluted the CH2Cl2 (100 mL) and washed with H2O (2×100 mL). The organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound as a yellow oil, (5.6 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 2 hours
  3. customThe cooled reaction mixture
  4. washwashed with H2O (2×100 mL)
  5. dry with materialThe organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fc30129e402e4fdc8487e66d8df0f5ec
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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