Hydroxybenzenesulfonic acid → HCID 86641481, compound

HRID 1518103Notes

Reaction equation

HRID 1518103 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>CC(O)C>[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

4

Reactant 2

HCID 15619088Hydroxybenzenesulfonic acidHCID 44182694HCID 44182694, compound

Product 1

HCID 86641481HCID 86641481, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of the compound (1.00 g, 2.0 mmol) obtained in Example 3 and benzenesulfonic acid monohydrate (316 mg, 2.0 mmol) in 2-propanol (5 mL) was heated to 70° C. The dissolution of the solid matter was confirmed, and the solution was then stirred with cooling to room temperature over 4 hours. The resulting precipitate was collected by filtration, then washed with 2-propanol (1 mL×2), and then dried under reduced pressure to obtain a crude product of the title compound (1.13 g). A 500 mg aliquot thereof was added to a mixed solution of acetone (10 mL) and water (100 μL), and the mixture was heated. The dissolution thereof was confirmed, and the solution was then gradually cooled and stirred at 35 to 40° C. for 1 hour. Then, the solution was further cooled and stirred at 20 to 25° C. for 1 hour. The precipitate was collected by filtration and washed with acetone (1 mL) to obtain the title compound (323 mg).

Workup

  1. dissolutionThe dissolution of the solid matter
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with 2-propanol (1 mL×2)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-a0cfaae483664587909446d8764b386a
Source dataset
uspto-grants-2012_07
Patent number
US08232405B2

Reaction notes

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