4-Chloro-3-nitrobenzenesulfonamide → HCID 67126583, compound

HRID 706928Notes

Reaction equation

HRID 706928 reaction equation
Cl[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].[F:15][CH2:16][CH:17]([N:20]1[CH2:23][CH:22]([NH2:24])[CH2:21]1)[CH2:18][F:19].C(NC(C)C)(C)C>O1CCOCC1>[F:15][CH2:16][CH:17]([N:20]1[CH2:23][CH:22]([NH:24][C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:21]1)[CH2:18][F:19]

Participants

5

Reactant 3

HCID 73244-Chloro-3-nitrobenzenesulfonamideHCID 7912DiisopropylamineHCID 67126718HCID 67126718, compound

Product 1

HCID 67126583HCID 67126583, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 4-chloro-3-nitrobenzenesulfonamide (0.225 g) and 1-(1,3-difluoropropan-2-yl)azetidin-3-amine (0.193 g) in dioxane (5 mL) was added diisopropylamine (0.832 mL). The reaction was sonicated and then heated to 100° C. After stirring overnight, the reaction was concentrated and loaded onto silica gel (GraceResolv 12 g) and eluted with a gradient of 0.5% to 3.5% methanol/dichloromethane to give the title compound.

Workup

  1. customThe reaction was sonicated
  2. concentrationthe reaction was concentrated
  3. washeluted with a gradient of 0.5% to 3.5% methanol/dichloromethane

Sources & evidence

ORD record
ord-836d93ebb294428ba83a8b48e9fb7cd2
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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