Hydrochloric Acid → HCID 59469955, compound

HRID 1502196Notes

Reaction equation

HRID 1502196 reaction equation
C([N:4]1[C:16]2[CH:15]=[CH:14][C:13]([Si:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[C:8]([Si:36]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH:9]=2)(=O)C.[OH-].[Na+].Cl>O1CCCC1>[C:30]1([Si:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:13]2[CH:14]=[CH:15][C:16]3[NH:4][C:5]4[C:10]([C:11]=3[CH:12]=2)=[CH:9][C:8]([Si:36]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[CH:7][CH:6]=4)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86676047HCID 86676047, compound

Product 1

HCID 59469955HCID 59469955, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The obtained 9-acetyl-3,6-bis(triphenylsilyl)carbazole (1.97 g) was dissolved in tetrahydrofuran (50 mL). A 50% by mass aqueous sodium hydroxide solution (1.1 g) was added to the solution. The resultant mixture was stirred at 50° C. for 3 hours and cooled to room temperature. Diluted hydrochloric acid was added thereto until the pH reached 5, followed by stirring for 30 min. The mixture was extracted with methylene chloride. The separated organic layer was washed with water and dried, and the methylene chloride was evaporated. The residue was purified with a recycle HPLC (name of apparatus: Recycling Preparative HPLC LC-9201, product of Japan Analytical Industry Co., Ltd., developing solvent: THF, flow rate: 3.5 mL/min), to thereby obtain 1.28 g of 3,6-bis(triphenylsilyl)carbazole as colorless powder.

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. washThe separated organic layer was washed with water
  3. customdried
  4. customthe methylene chloride was evaporated
  5. customThe residue was purified with a recycle HPLC (name of apparatus: Recycling Preparative HPLC LC-9201, product of Japan Analytical Industry Co., Ltd., developing solvent: THF, flow rate: 3.5 mL/min)

Sources & evidence

ORD record
ord-86413646ef934f639cf9627e456002ef
Source dataset
uspto-grants-2015_12
Patent number
US09206202B2

Reaction notes

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