Dimethyl Sulfoxide → HCID 66916056, compound

HRID 2061428Notes

Reaction equation

HRID 2061428 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[S:11]([NH2:14])(=[O:13])=[O:12].CS(C)=O.[CH2:19]([NH:21][CH2:22]C)C.[F-].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.O>[CH3:19][N:21]([CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[S:11]([NH2:14])(=[O:13])=[O:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8021DiethylamineHCID 522689Potassium FluorideHCID 4462806089581-71-5

Product 1

HCID 66916056HCID 66916056, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-chloro-6-nitro-benzenesulfonamide (500 mg, 2.10 mmol), DMSO (3 ml), diethyl amine (10 ml of 2 M solution in THF), Bu4NHSO4 (34 mg, 0.1 mmol) and KF (58 mg, 1.0 mmol) is heated in an autoclave at 70° C. for 16 h. The mixture is diluted with water and extracted with CH2Cl2. The solvent is removed and the residue subjected to chromatography (SiO2, TBME/cyclohexane 1:9→TBME) to give 2-dimethylamino-6-nitro-benzenesulfonamide as a colorless solid.

Workup

  1. extractionextracted with CH2Cl2
  2. customThe solvent is removed

Sources & evidence

ORD record
ord-5de8ee561dcd469ea9c3def653edc9e1
Source dataset
uspto-grants-2012_10
Patent number
US08283356B2

Reaction notes

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