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

HRID 2168114Notes

Reaction equation

HRID 2168114 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-307a0ffa1d264d6e847004d3cecab197
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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