Trifluoroacetic acid → N,N-bis(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide

HRID 85567Notes

Reaction equation

HRID 85567 reaction equation
[O:1]=[S:2]1(=[O:23])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][NH:10][S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])(=[O:13])=[O:12])[CH2:4][CH2:3]1.O[CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][S:30](=[O:34])(=[O:33])[CH2:29][CH2:28]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C(O)(C(F)(F)F)=O>C1COCC1>[O:23]=[S:2]1(=[O:1])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]([CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][S:30](=[O:34])(=[O:33])[CH2:29][CH2:28]2)[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])(=[O:12])=[O:13])[CH2:4][CH2:3]1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 218748114-(2-Hydroxyethyl)-1lambda~6~,4-thiazinane-1,1-dioneHCID 68358008N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide

Product 1

HCID 68275931N,N-bis(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamideYield 119.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide (0.500 g, 1.38 mmol) was combined with 4-(2-hydroxyethyl)thiomorpholine 1,1-dioxide (0.296 g, 1.65 mmol) in THF (10 mL). To this mixture was added triphenylphosphine (0.541 g, 2.06 mmol) and diethyl azodicarboxylate (0.359 g, 2.06 mmol). The resulting mixture was stirred at rt for 72 h. The mixture was concentrated in vacuo, then redissolved in acetonitrile. Purification by reverse phase preparative HPLC gave the title compound as a pale yellow solid (0.863 g, 83% yield) bis-TFA salt. LCMS: m/z 525 (M+H+), retention time 1.25 min (method 11). 1H NMR (500 MHz, MeOD) δ ppm 2.85 (t, J=6.71 Hz, 4H) 3.14 (d, J=5.49 Hz, 8H) 3.18 (d, J=5.80 Hz, 8H) 3.51 (t, J=6.71 Hz, 4H) 7.71-7.75 (m, 1H) 7.75-7.84 (m, 2H) 8.05 (d, J=7.63 Hz, 1H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionredissolved in acetonitrile
  3. customPurification by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-95f934cd6085467084aa52646123ea21
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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