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Triethylamine → HCID 22710634, compound

HRID 352799
Notes
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Reaction equation

HRID 352799 reaction equation
Cl.[CH2:2]([CH:4]1[CH2:9][NH:8][CH2:7][CH2:6][NH:5]1)[CH3:3].[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21])[C:15]([S:29](Cl)(=[O:31])=[O:30])=[CH:14]2.C(N(CC)CC)C>C(Cl)Cl.O>[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:21])=[O:22])[C:15]([S:29]([N:8]1[CH2:7][CH2:6][NH:5][CH:4]([CH2:2][CH3:3])[CH2:9]1)(=[O:31])=[O:30])=[CH:14]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 227107862-Ethyl piperazine hydrochlorideHCID 235137375-Chloro-1-phenylsulfonylindole-2-sulfonyl chloride

Product 1

HCID 22710634HCID 22710634, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a methylene chloride solution (700 ml) of 2-ethylpiperazine hydrochloride (5.00 g) were added 5-chloro -1-phenylsulfonylindol-2-sulfonyl chloride (7.14 g) and triethylamine (11.16 ml) and the resulting mixture was stirred at room temperature for 3 hours. Distilled water and methylene chloride were added and the water layer was extracted three times. The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (methanol:methylene chloride=1:100), whereby the title compound (5.86 g) was obtained as a pale yellow oil.

Workup

  1. extractionthe water layer was extracted three times
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent
  5. customThe residue was purified by chromatography on a silica gel column (methanol:methylene chloride=1:100), whereby the title compound (5.86 g)
  6. customwas obtained as a pale yellow oil

Sources & evidence

ORD record
ord-2e43c9c5b2634f2894a5c3b3f9cd452b
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06747023B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes