Triethylamine → N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide

HRID 85559Notes

Reaction equation

HRID 85559 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][S:7](=[O:11])(=[O:10])[CH2:6][CH2:5]1.C(N(CC)CC)C.[N+:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28](Cl)(=[O:30])=[O:29])([O-:21])=[O:20]>C(Cl)Cl>[O:10]=[S:7]1(=[O:11])[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:1][S:28]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N+:19]([O-:21])=[O:20])(=[O:29])=[O:30])[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 27606184-(2-Aminoethyl)-1lambda~6~,4-thiazinane-1,1-dione

Product 1

HCID 68358008N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamideYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(2-aminoethyl)thiomorpholine 1,1-dioxide (2.00 g, 11.2 mmol) and triethylamine (1.42 g, 14.0 mmol) in DCM (100 mL) was cooled in an ice bath and treated slowly with 2-nitrobenzene-1-sulfonyl chloride (2.49 g, 11.2 mmol). The mixture was removed from the ice bath and stirred at rt for 18 h. The resulting mixture was washed with water (2×50 mL) and the combined aqueous washes were extracted with DCM (50 mL). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to a yellow solid. Purification by silica gel chromatography (linear gradient 100% DCM to 100:1 DCM:MeOH) gave the title compound as a pale yellow solid (3.47 g, 85% yield). LCMS: m/z 364 (M+H+), retention time 0.98 min (method 11). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 2.71 (t, J=5.49 Hz, 2H) 2.96 (br. s., 4H) 3.05 (br. s., 4H) 3.20 (q, J=5.49 Hz, 2H) 5.93 (br. s., 1H) 7.73-7.84 (m, 2H) 7.84-7.93 (m, 1H) 8.11-8.23 (m, 1H).

Workup

  1. temperaturewas cooled in an ice bath
  2. customThe mixture was removed from the ice bath
  3. washThe resulting mixture was washed with water (2×50 mL)
  4. extractionthe combined aqueous washes were extracted with DCM (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a yellow solid
  8. customPurification by silica gel chromatography (linear gradient 100% DCM to 100:1 DCM:MeOH)

Sources & evidence

ORD record
ord-ccbafdee95db4706834f5a4b40b2aceb
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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