Triethylamine → HCID 68290538, compound

HRID 2205894Notes

Reaction equation

HRID 2205894 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([O:27][CH3:28])[CH:19]=1>C1COCC1>[CH3:28][O:27][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[N+:24]([O-:26])=[O:25])[CH2:17][N:1]1[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6484228Thiomorpholine 1,1-dioxideHCID 126216043-Methoxy-4-nitrobenzyl bromide

Product 1

HCID 68290538HCID 68290538, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thiomorpholine 1,1-dioxide (0.242 g, 1.788 mmol) and triethylamine (0.19 mL, 1.341 mmol) were added to a solution of 4-(bromomethyl)-2-methoxy-1-nitrobenzene (Preparation 74, 0.22 g, 0.894 mmol) in THF (2.2 mL). The reaction mixture was stirred overnight at room temperature before being concentrated under reduced pressure and purified via Biotage silica gel column chromatography eluting with (DCM/EtOAc 99/1 to 90/10) to afford the title product as a white solid (242 mg, 90%). 1H NMR (500 MHz, CDCl3): δ 3.00-3.04 (m, 4H), 3.09-3.12 (m, 4H), 3.71 (s, 2H), 3.98 (s, 3H), 7.01 (m, 1H), 7.09 (m, 1H), 7.84 (d, J=8.2 Hz, 1H). LC (Method C)-MS (ESI, m/z) tR 2.03 min, 301 [(M+H+), 100%].

Workup

  1. concentrationbefore being concentrated under reduced pressure
  2. custompurified via Biotage silica gel column chromatography
  3. washeluting with (DCM/EtOAc 99/1 to 90/10)

Sources & evidence

ORD record
ord-de907ea1babf40c58246c0dc7dcb22b8
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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