Hydroxybenzenesulfonic acid → HCID 86641481, compound

HRID 561089Notes

Reaction equation

HRID 561089 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[O:21][CH2:20][CH2:19][C:18]4=[O:25])[CH2:9][CH2:8]2)=[CH:4][C:3]=1[O:28][CH2:29][CH2:30][O:31][CH3:32].O.[C:34]1([S:40]([OH:43])(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[C:34]1([S:40]([OH:43])(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[O:21][CH2:20][CH2:19][C:18]4=[O:25])[CH2:9][CH2:8]2)=[CH:4][C:3]=1[O:28][CH2:29][CH2:30][O:31][CH3:32]

Participants

3

Reactant 2

HCID 15619088Hydroxybenzenesulfonic acidHCID 44182694HCID 44182694, compound

Product 1

HCID 86641481HCID 86641481, compoundYield 88%

Conditions

Temperature
42.5 °C

Procedure

The compound (7.76 g, 15.5 mmol) obtained in Example 3 was dissolved in 1% (v/v) hydrated acetone (100 mL), and the solution was warmed to 40 to 45° C. Then, benzenesulfonic acid monohydrate (2.93 g, 17 mmol) was added thereto, and the mixture was stirred. The dissolution of the solid matter was confirmed. Then, a seed crystal (50 mg) was added thereto, and the mixture was stirred at 40 to 45° C. for 1 hour. Subsequently, the mixture was stirred with cooling to 25° C. over 3 hours and then stirred at room temperature for 17.5 hours. Subsequently, the mixture was cooled to 5° C. or lower over 1 hour and stirred at this temperature for 1 hour. The precipitation was collected by filtration, and the residue on the filter was washed with cold acetone (10 mL×2) and then dried under reduced pressure to obtain the title compound (8.83 g, 88%) as a colorless crystalline solid.

Workup

  1. dissolutionThe dissolution of the solid matter
  2. stirringthe mixture was stirred at 40 to 45° C. for 1 hour
  3. stirringSubsequently, the mixture was stirred
  4. temperaturewith cooling to 25° C. over 3 hours
  5. stirringstirred at room temperature for 17.5 hours
  6. temperatureSubsequently, the mixture was cooled to 5° C. or lower over 1 hour
  7. stirringstirred at this temperature for 1 hour
  8. customThe precipitation
  9. filtrationwas collected by filtration
  10. washthe residue on the filter was washed with cold acetone (10 mL×2)
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-efcdac25278d4589b599490fcdba56d0
Source dataset
uspto-grants-2011_11
Patent number
US08063223B2

Reaction notes

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