Acetone → HCID 69689811, compound

HRID 321973Notes

Reaction equation

HRID 321973 reaction equation
[K:1].[C:2]1([S:8]([NH:11][C:12](=[O:36])[C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:26][CH:25]=3)[CH:14]=2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[K+].CO.CC(C)=O>[Pd].O>[K:1].[C:2]1([S:8]([NH:11][C:12](=[O:36])[C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[CH:26][CH:25]=3)[CH:14]=2)(=[O:9])=[O:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 516893Potassium BicarbonateHCID 69689666HCID 69689666, compound

Product 1

HCID 69689811HCID 69689811, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

5% palladium/carbon (0.64 g) is added to a mixture of N-benzenesulfonyl-3-(biphenyl-4-ylmethylamino)-4-nitrobenzamide potassium salt (4.27 g), 20% potassium bicarbonate aqueous solution (10.7 g), and methanol (200 ml). The solution is then stirred for 14 hours at 35° C. under a hydrogen environment. The precipitated crystals are dissolved when a mixture solution of acetone and water (acetone/water=5/2, 400 ml) is added and its solids are separated through filtration. The filtrate is concentrated, the precipitated crystals are separated through filtration and are dried. Thus, N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino)benzamide potassium salt (3.15 g) is obtained.

Workup

  1. additionis added
  2. customits solids are separated through filtration
  3. concentrationThe filtrate is concentrated
  4. customthe precipitated crystals are separated through filtration
  5. customare dried

Sources & evidence

ORD record
ord-8e405134aaf34c81a849de287a240a75
Source dataset
uspto-grants-2001_04
Patent number
US06211177B1

Reaction notes

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