1-Bromo-3-chloropropane → HCID 57517460, compound

HRID 1842461Notes

Reaction equation

HRID 1842461 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][CH2:26][Cl:27]>CC(C)=O>[Cl:27][CH2:26][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:11])=[O:12]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 5461210HCID 5461210, compound

Product 1

HCID 57517460HCID 57517460, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 2-nitro-N-(prop-2-yn-1-yl)benzenesulfonamide (1.08 g, 4.48 mmol) and cesium carbonate (7.30 g, 22.42 mmol) in acetone (40 mL) was added neat 1-bromo-3-chloropropane (6.5 mL, 66 mmol) dropwise. Upon complete addition, the reaction mixture was stirred at room temperature for 2 days. 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 Intermediate 18 as an oil (0.9764 g, 69%). 1H NMR (400 MHz, CDCl3) δ 8.10-8.05 (m, 1H), 7.76-7.62 (m, 3H), 4.22 (d, J=2.5 Hz, 2H), 3.57 (td, J=6.6, 2.9 Hz, 4H), 2.21 (t, J=2.5 Hz, 1H), 2.14-2.06 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-279ebb0da575453996ba4ea3e0f97c31
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

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