Triethylamine → HCID 66962049, compound

HRID 1359954Notes

Reaction equation

HRID 1359954 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH2:17])=[CH:11][CH:10]=1.[N+:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27](Cl)(=[O:29])=[O:28])([O-:20])=[O:19].C(=O)([O-])O.[Na+]>O1CCCC1>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][S:27]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N+:18]([O-:20])=[O:19])(=[O:28])=[O:29])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 533915p-Bromophenethylamine

Product 1

HCID 66962049HCID 66962049, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine 0.7 ml (5.0 mmol) was added to a solution of 500 mg (2.5 mmol) of 2-(4-bromophenyl)ethanamine in tetrahydrofuran (5 ml). 2-Nitrobenzenesulfonyl chloride (664.6 mg, 3.0 mmol) was then added thereto, and the mixture was stirred at room temperature for one hr. Thereafter, a saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and was then filtered. The filtrate was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to give 915 mg (yield 95%) of the title compound.

Workup

  1. extractionthe mixture was then extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationwas then filtered
  4. concentrationThe filtrate was concentrated under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-ddea5eb837814192b058dd4b4eb73426
Source dataset
uspto-grants-2011_02
Patent number
US07879808B2

Reaction notes

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