Sulfuric Acid → HCID 86672519, compound

HRID 1915093Notes

Reaction equation

HRID 1915093 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([O:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([Cl:32])=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=3)=[O:20])=[CH:16][CH:17]=2)[CH:8]=[CH:9][N:10]=1)=[O:4].[S:33](=[O:37])(=[O:36])([OH:35])[OH:34]>C(O)C>[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([Cl:32])=[C:26]([C:28]([F:31])([F:29])[F:30])[CH:27]=3)=[O:20])=[CH:14][CH:13]=2)[CH:8]=[CH:9][N:10]=1)=[O:4].[S:33]([O-:37])([O-:36])(=[O:35])=[O:34]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 216239Sorafenib

Product 1

HCID 86672519HCID 86672519, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethanol (25 mL) was added to a reaction vessel containing sorafenib free base (5 g). The reaction mixture was stirred for about 5 minutes. The temperature was raised to about 60° C. The reaction mixture was stirred for about 30 minutes. A sulphuric acid solution (sulphuric acid:ethanol:water: 0.57 mL:6 mL:19 mL) was added drop-wise. The reaction mixture was cooled to room temperature and stirred for about 12 hours. The reaction mixture was concentrated. The solid was filtered and dried under reduced pressure at about 50° C. for about 12 hours to obtain sorafenib sulphate.

Workup

  1. stirringThe reaction mixture was stirred for about 30 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. stirringstirred for about 12 hours
  4. concentrationThe reaction mixture was concentrated
  5. filtrationThe solid was filtered
  6. customdried under reduced pressure at about 50° C. for about 12 hours

Sources & evidence

ORD record
ord-09a9735f38414e9baae1cc92bfa412fe
Source dataset
uspto-grants-2013_12
Patent number
US08614329B2

Reaction notes

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