1-Bromo-2-Chloroethane → HCID 57517459, compound

HRID 1842458Notes

Reaction equation

HRID 1842458 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH2:14][C:15]#[CH:16])(=[O:12])=[O:11])([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:24][CH2:25][Cl:26]>CC(C)=O>[Cl:26][CH2:25][CH2:24][N:13]([CH2:14][C:15]#[CH:16])[S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 10796Cesium carbonateHCID 5461210HCID 5461210, compound

Product 1

HCID 57517459HCID 57517459, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 2-nitro-N-(prop-2-yn-1-yl)benzenesulfonamide (0.448 g, 1.86 mmol) and cesium carbonate (1.75 g, 5.37 mmol) in acetone (10 mL) was added neat 1-bromo-2-chloroethane (0.775 mL, 9.31 mmol) dropwise. The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was concentrated and the residue partitioned between EtOAc (25 mL) and water (15 mL). The aqueous layer was extracted with additional EtOAc (20 mL), the combined organic layers dried over anhydrous MgSO4 and concentrated. Purification via silica chromatography (25-40% EtOAc/hexane) afforded an oil (0.540 g, 96%). LC-MS: (FA) ES+303. 1H NMR (400 MHz, CDCl3) δ 8.08 (dt, J=8.2, 3.7 Hz, 1H), 7.77-7.64 (m, 3H), 4.30 (d, J=2.5 Hz, 2H), 3.78-3.68 (m, 4H), 2.23 (t, J=2.5 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between EtOAc (25 mL) and water (15 mL)
  3. extractionThe aqueous layer was extracted with additional EtOAc (20 mL)
  4. dry with materialthe combined organic layers dried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customPurification via silica chromatography (25-40% EtOAc/hexane)

Sources & evidence

ORD record
ord-b7899afb9fb34c6d94ca512421b6a923
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

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