Triethylamine → Benzenesulfonamide, 2-nitro-N-(tetrahydro-2H-thiopyran-4-yl)-

HRID 239908Notes

Reaction equation

HRID 239908 reaction equation
Cl.[S:2]1[CH2:7][CH2:6][CH:5]([NH2:8])[CH2:4][CH2:3]1.C(N(CC)CC)C.[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26])([O-:18])=[O:17]>C1COCC1>[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([NH:8][CH:5]1[CH2:6][CH2:7][S:2][CH2:3][CH2:4]1)(=[O:27])=[O:26])([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 18331311Thian-4-amine--hydrogen chloride (1/1)

Product 1

HCID 70967975Benzenesulfonamide, 2-nitro-N-(tetrahydro-2H-thiopyran-4-yl)-Yield 92.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
13 °C

Procedure

To a suspension of tetrahydro-2H-thiopyran-4-amine hydrochloride (80.0 g) in THF (800 mL) were added triethylamine (239 mL) and 2-nitrobenzenesulfonyl chloride (126.9 g) under ice-cooling at an inside temperature of 2-24° C., and the mixture was stirred at room temperature for 23 hr. The reaction solution was partitioned and extracted with ethyl acetate and water, and the organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to the extent crystals do not precipitate and purified by silica gel column chromatography [eluent; hexane:ethyl acetate=50:50 (volume ratio)]. The obtained solid was washed with ethanol-diisopropyl ether (1:4), and dried under reduced pressure to give the title compound (145.6 g, yield 92%) as a pale-green solid.

Workup

  1. customThe reaction solution was partitioned
  2. extractionextracted with ethyl acetate and water
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure to the extent crystals
  6. customdo not precipitate
  7. custompurified by silica gel column chromatography [eluent; hexane:ethyl acetate=50:50 (volume ratio)]
  8. washThe obtained solid was washed with ethanol-diisopropyl ether (1:4)
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-ff010d1f6948419d9cdd06dba409b078
Source dataset
uspto-grants-2014_02
Patent number
US08642770B2

Reaction notes

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