Phosphoric Acid → HCID 19957363, compound

HRID 55366Notes

Reaction equation

HRID 55366 reaction equation
[P:1](=[O:5])([OH:4])([OH:3])[OH:2].[N:6]1([NH:12][C:13]([C:15]2[C:19]([CH3:20])=[C:18]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[N:17]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[Cl:35])[N:16]=2)=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>CC(CC)=O>[P:1]([OH:5])([OH:4])([OH:3])=[O:2].[N:6]1([NH:12][C:13]([C:15]2[C:19]([CH3:20])=[C:18]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)[N:17]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[Cl:35])[N:16]=2)=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 104850Rimonabant

Product 1

HCID 19957363HCID 19957363, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4.61 g of 85% phosphoric acid are added at 20°±3° C. to a solution of 18.55 g of the compound obtained in example 195 in 185 ml of methylethylketone. Water is removed by distillation under atmospheric pressure of the azeotrope methylethylketone/water. The mixture is progressively cooled to 20°±3° C. while stirring for 20 hours. The white crystals formed are filtered off, washed with methylethylketone and dried under vacuum to give 21 g of the expected product. DSC: endothermic peak centered at 185.5° C.

Workup

  1. customWater is removed by distillation under atmospheric pressure of the azeotrope methylethylketone/water
  2. temperatureThe mixture is progressively cooled to 20°±3° C.
  3. customThe white crystals formed
  4. filtrationare filtered off
  5. washwashed with methylethylketone
  6. customdried under vacuum

Sources & evidence

ORD record
ord-75839fdd01854b08bbc9948c19bbf570
Source dataset
uspto-grants-1997_04
Patent number
US05624941

Reaction notes

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