Diisopropylethylamine → 4-(1,4-Dioxaspiro[4.5]decan-8-ylamino)-3-nitrobenzenesulfonamide

HRID 574931Notes

Reaction equation

HRID 574931 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[O:15]1[C:19]2([CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]2)[O:18][CH2:17][CH2:16]1.C(N(C(C)C)CC)(C)C>O1CCCC1.C(OCC)(=O)C>[O:15]1[C:19]2([CH2:24][CH2:23][CH:22]([NH:25][C:2]3[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=3[N+:12]([O-:14])=[O:13])[CH2:21][CH2:20]2)[O:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 146343151,4-Dioxaspiro[4.5]decan-8-amineHCID 167824874-Fluoro-3-nitrobenzenesulfonamide

Product 1

HCID 671269854-(1,4-Dioxaspiro[4.5]decan-8-ylamino)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-fluoro-3-nitrobenzenesulfonamide (1.4 g) in tetrahydrofuran (30 mL) was added 1,4-dioxaspiro[4.5]decan-8-amine (1.0 g) and diisopropylethylamine (5 mL). The mixture was stirred overnight. The mixture was diluted with ethyl acetate (300 mL) and washed with water, brine and dried over Na2SO4. Filtration and evaporation of the solvent gave the title compound.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-16f94fa34b794aaab02b4f2557be408c
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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