Hydrochloric Acid → HCID 54489016, compound

HRID 1681558Notes

Reaction equation

HRID 1681558 reaction equation
Cl[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]=1[C:9](=[O:21])[C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][C:11]=1[Cl:20].[CH3:22][NH:23][CH2:24][CH2:25][NH:26][CH3:27].C(N([CH2:33][CH3:34])CC)C.[ClH:35]>C(Cl)Cl>[CH3:22][N:23]([C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]=1[C:9](=[O:21])[C:34]1[CH:33]=[CH:14][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:12][C:11]=1[Cl:35])[CH2:24][CH2:25][N:26]([CH3:27])[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]=1[C:9](=[O:21])[C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][C:11]=1[Cl:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8070N,N'-DimethylethylenediamineHCID 8471TriethylamineHCID 142799823-Chloro-2-[2-chloro-4-(methanesulfonyl)benzoyl]cyclohex-2-en-1-one

Product 1

HCID 54489016HCID 54489016, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Chloro-2-(2-chloro-4-methanesulfonylbenzoyl) -cyclohex-2-enone (1.8 g., 5 millimole) was dissolved in 50 ml of methylene chloride and stirred at room temperature. A mixture of N,N'-dimethylethylene diamine (0.22 g., 2.5 mmol mole) and triethylamine (0.5 g., 5 mml) in 10 ml of methylene chloride was added dropwise over 20 minutes and the resulting solution was stirred for 2 hours. The reaction mixture was poured into lN HCl and extracted with additional methylene chloride. The organic layer was washed with saturated NaHCO3 solution, dried with MgSO4 and the solvent evaporated to yield a yellow foam: 1.6 g., 86%. The structure is consistent with nuclear magnetic resonance, infrared and mass spectral data.

Workup

  1. additionwas added dropwise over 20 minutes
  2. stirringthe resulting solution was stirred for 2 hours
  3. extractionextracted with additional methylene chloride
  4. washThe organic layer was washed with saturated NaHCO3 solution
  5. dry with materialdried with MgSO4
  6. customthe solvent evaporated
  7. customto yield a yellow foam

Sources & evidence

ORD record
ord-83ef7a2d6c4c4caebff1c4bdd4260f83
Source dataset
uspto-grants-1992_12
Patent number
US05173105

Reaction notes

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