4-Nitrobenzenesulfonyl chloride → HCID 22997215, compound

HRID 29197Notes

Reaction equation

HRID 29197 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([O:7][NH:8]O)[CH2:3][CH2:2]1.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)([O-:12])=[O:11].C(N(C(C)C)CC)(C)C.NN>C1COCC1.C(OCC)(=O)C>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([S:19]([NH:8][O:7][CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)(=[O:21])=[O:20])=[CH:17][CH:18]=1)([O-:12])=[O:11]

Participants

7

Reactant 4

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 569763924-Tetrahydropyranoxyhydroxylamine

Product 1

HCID 22997215HCID 22997215, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-tetrahydropyranoxyhydroxylamine (33.2 mmol, 3.77 g) and 4-nitrobenzenesulfonylchloride (38.6 mmol, 8.56 g) were combined in anhydrous THF (100 mL) with diisopropylethylamine (69.3 mmol, 11.2 mL). The reaction was stirred at room temperature for 48 hours. Hydrazine (2 mL) was injected to the stirring solution to break-up the bisarylsulfonamide dimer biproduct. The reaction was stirred for an additional 24 hours. The reaction was diluted in ethyl acetate, washed in brine, filtered to remove insoluble solids and concentrated. The crude was purified by crystallization from hot ethyl acetate to provide 3.5 g (36%) of white crystals. Rf=0.3 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 8.42 (2H,d), 8.13 (2H,d), 6.93 (1H,s), 4.27 (1H,m), 3.91 (2H,m), 3.45 (2H,m), 2.02 (2H,m), 1.61 (2H,m).

Workup

  1. stirringThe reaction was stirred for an additional 24 hours
  2. washwashed in brine
  3. filtrationfiltered
  4. customto remove insoluble solids
  5. concentrationconcentrated
  6. customThe crude was purified by crystallization from hot ethyl acetate

Sources & evidence

ORD record
ord-340a7d80214a4753a46f9f47e635ef19
Source dataset
uspto-grants-2008_09
Patent number
US07419967B2

Reaction notes

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