HCID 15670670, compound → HCID 15680278, compound

HRID 1647024Notes

Reaction equation

HRID 1647024 reaction equation
O[CH2:2][C:3]([NH:6][C:7]([C:9]1[C:10]([C:18]2[C:19]([C:27]([NH:29][C:30]([CH3:34])([CH2:32][OH:33])[CH3:31])=O)=[CH:20][CH:21]=[C:22]3[O:26][CH2:25][O:24][C:23]=23)=[C:11]2[O:17][CH2:16][O:15][C:12]2=[CH:13][CH:14]=1)=[O:8])([CH3:5])[CH3:4]>S(Cl)(Cl)=O>[CH2:25]1[O:24][C:23]2[C:18]([C:10]3[C:11]4[O:17][CH2:16][O:15][C:12]=4[CH:13]=[CH:14][C:9]=3[C:7]3[O:8][CH2:2][C:3]([CH3:5])([CH3:4])[N:6]=3)=[C:19]([C:27]3[O:33][CH2:32][C:30]([CH3:31])([CH3:34])[N:29]=3)[CH:20]=[CH:21][C:22]=2[O:26]1

Participants

3

Reactant 1

HCID 15670670HCID 15670670, compound

Product 1

HCID 15680278HCID 15680278, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

N,N'-Bis(3-hydroxy-2-methylpropan-2-yl)-5,6-methylenedioxy-5',6'-methylenedioxy-2,2'-biphenyldicarboxamide (3 g) is added to thionyl chloride (20 ml), and the mixture is stirred at room temperature for 2 hours. The reaction mixture is distilled under reduced pressure to remove thionyl chloride, and the residue is dissolved in ethyl acetate. The solution is washed, dried and distilled to remove the solvent, and the residue is crystallized from diisopropyl ether to give 5,6-methylenedioxy-5',6'-methylenedioxy-2,2'-bis(4,4-dimethyl-4,5-dihydro-2-oxazolyl)biphenyl (2 g) as colorless crystal. M.p. 152°-154° C.

Workup

  1. distillationThe reaction mixture is distilled under reduced pressure
  2. customto remove thionyl chloride
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washThe solution is washed
  5. customdried
  6. distillationdistilled
  7. customto remove the solvent
  8. customthe residue is crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-20e6ba66cd984ee29d3be894c7f0e241
Source dataset
uspto-grants-1993_01
Patent number
US05182404

Reaction notes

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