Thiomorpholine → 2-(4-Thiomorpholinyl)-3-pyridinesulfonamide

HRID 542388Notes

Reaction equation

HRID 542388 reaction equation
Cl[C:2]1[C:7]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][S:15][CH2:14][CH2:13]1>CN(C)C=O>[N:12]1([C:2]2[C:7]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:17][CH2:16][S:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 67164Thiomorpholine2×HCID 122344452-chloropyridine-3-sulfonamide

Product 1

HCID 201601252-(4-Thiomorpholinyl)-3-pyridinesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a dry flask under an inert nitrogen atmosphere was mixed 2.5 g of 2-chloro-3-pyridinesulfonamide, 100 mL of dry N,N-dimethylformamide (DMF), and 2.7 mL of thiomorpholine. The mixture was heated at 80° C. overnight at which time an additional 0.3 mL of thiomorpholine was added and the heating was continued. After 24 hours the mixture was concentrated and the residue was taken up in THF. The solids were filtered and the filtrate was concentrated and chromatographed on silica gel using 1:1 ethyl acetate/hexane as eluent. The pure subject compound was isolated as a solid, which melted at 176°-177° C.; NMR (200 MHz, CDCl3): δ 2.89 (m, CH2S, 4H), 3.45 (m, CH2N, 4H), 5.52 (s, NH2, 2H), 7.26 (t, ArH, 1H), 8.2-8.6 (m, ArH, 2H).

Workup

  1. additionwas added
  2. concentrationAfter 24 hours the mixture was concentrated
  3. filtrationThe solids were filtered
  4. concentrationthe filtrate was concentrated
  5. customchromatographed on silica gel using 1:1 ethyl acetate/hexane as eluent
  6. customThe pure subject compound was isolated as a solid, which melted at 176°-177° C.

Sources & evidence

ORD record
ord-69fd602922434efcb18e3e29b2a4c670
Source dataset
uspto-grants-1987_04
Patent number
US04657578

Reaction notes

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