Tributylstannane → HCID 10878603, compound

HRID 1776180Notes

Reaction equation

HRID 1776180 reaction equation
Br[CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]2[S:5](=[O:7])(=[O:6])[NH:4][CH2:3][CH2:2][C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 2774570N-(2-bromoethyl)-4-chlorobenzenesulfonamide

Product 1

HCID 10878603HCID 10878603, compoundYield 4.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A two-necked flask equipped with a condenser and a rubber septum was charged with N-(2-bromoethyl)-4-chlorobenzenesulfonamide (2.80 g, 9.4 mmol) and anhydrous benzene (50 mL). The reaction vessel was degassed and backfilled with argon and then heated to reflux. Under reflux, a solution of tributyltin hydride (5.05 mL, 18.8 mmol) and 2,2′-azobis(2-methylpropionitrile) (0.77 g, 4.7 mmol) in anhydrous benzene (25 mL) was added slowly over 8 hours using a syringe pump, and the mixture was refluxed for a further 12 hours. After cooling, the reaction mixture was concentrated and the residue purified by silica gel column chromatography (0-40% ethyl acetate in methylene chloride) followed by preparative TLC (1:2 ethyl acetate in hexanes) to afford the pure product as a white foam (0.085 g, 4%). 1H NMR (300 MHz, CDCl3) δ 7.77 (d, 1H, J=8.4 Hz), 7.37 (dd, 1H, J=8.1, 2.1 Hz), 7.26 (s, 1H), 4.47 (t, 1H, J=7.5 Hz), 3.83 (dt, 2H, J=7.5, 6.0 Hz), 3.00 (t, 2H, J=6.0 Hz).

Workup

  1. customA two-necked flask equipped with a condenser
  2. customThe reaction vessel was degassed
  3. temperatureheated to reflux
  4. temperatureUnder reflux
  5. temperaturethe mixture was refluxed for a further 12 hours
  6. temperatureAfter cooling
  7. concentrationthe reaction mixture was concentrated
  8. customthe residue purified by silica gel column chromatography (0-40% ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-aea46e80d9fa4e5aa16ee09fe3110658
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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