Diisopropylethylamine → 4-(4-Iodobenzyl)thiomorpholine 1,1-dioxide

HRID 1961513Notes

Reaction equation

HRID 1961513 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][CH:4]=1.[NH:10]1[CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[CH2:12][CH2:11]1.CCN(C(C)C)C(C)C>C1COCC1>[I:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:10]2[CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[CH2:12][CH2:11]2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9542584-Iodobenzyl bromideHCID 6484228Thiomorpholine 1,1-dioxide

Product 1

HCID 582851564-(4-Iodobenzyl)thiomorpholine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(bromomethyl)-4-iodobenzene (1 g, 3.37 mmol), thiomorpholine 1,1-dioxide (0.546 g, 4.04 mmol) and DIPEA (0.882 mL, 5.05 mmol) were stirred in THF (15 mL) at room temperature overnight. The solvent was removed in vacuo while loading onto silica. Purification of the residue by MPLC (12-100% EtOAc-hexanes) gave 4-(4-iodobenzyl)thiomorpholine 1,1-dioxide as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customPurification of the residue by MPLC (12-100% EtOAc-hexanes)

Sources & evidence

ORD record
ord-905b96efb93c486e827d7e09bc522802
Source dataset
uspto-grants-2013_04
Patent number
US08415346B2

Reaction notes

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