Dichloromethane → HCID 68532958, compound

HRID 657546Notes

Reaction equation

HRID 657546 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:7](=[CH:8][CH:9]=1)[CH:6]([C:10]#[N:11])[CH2:5]2.ClCCl.C(N(CC)CC)C.[CH3:22][N:23]([CH3:28])[S:24](Cl)(=[O:26])=[O:25]>O>[CH3:22][N:23]([CH3:28])[S:24](=[O:26])(=[O:25])[O:1][C:2]1[CH:3]=[C:4]2[C:7](=[CH:8][CH:9]=1)[CH:6]([C:10]#[N:11])[CH2:5]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 12159643HCID 12159643, compound

Product 1

HCID 68532958HCID 68532958, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 g (13.8 mmoles) of 3-hydroxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile are mixed into 40 mL of dichloromethane, 3.9 g (2 equivalents) of triethylamine and 1.63 mL (1. 1 equivalents) of dimethylsulphamoyl chloride. Stirring is carried out at 25° C. for 4 days. The reaction mixture is poured into water, extracted with dichloromethane, dried over MgSO4, filtered and evaporated to obtain an oil. This residue is purified by flash chromatography over 70 g of silica (eluant: dichloromethane/toluene: 50/50). The expected product is obtained in the form of a white solid.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto obtain an oil
  6. customThis residue is purified by flash chromatography over 70 g of silica (eluant: dichloromethane/toluene: 50/50)

Sources & evidence

ORD record
ord-d1d0117bf2874eaf9d2558621b4a15b1
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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