Ammonium Chloride → 4-amino-N-isobutyl-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide

HRID 1049046Notes

Reaction equation

HRID 1049046 reaction equation
[CH2:1]([N:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]([F:27])([F:26])[F:25])[S:6]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH:2]([CH3:4])[CH3:3].[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([S:6]([N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]([F:27])([F:25])[F:26])(=[O:8])=[O:7])=[CH:10][CH:11]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86721890N-isobutyl-4-nitro-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide

Product 1

HCID 867218914-amino-N-isobutyl-N-(2-trifluoromethyl-phenyl)-benzenesulfonamideYield 98.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A partial solution of N-isobutyl-4-nitro-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide (1.68 g, 4.19 mmol), in EtOH (IMS grade, 50 mL) and water (15 mL) was treated with iron powder (˜325 mesh, 936 mg, 16.76 mmol) and ammonium chloride (896 mg, 16.76 mmol) and heated at reflux for 1 hour. The cooled mixture was filtered through diatomaceous earth washing the filter cake with EtOH and the filtrate concentrated to low volume under vacuum. The residue obtained was diluted with water and extracted into DCM. The combined extracts were dried over Na2SO4 and concentrated under vacuum. Purification by silica gel column chromatography (0-75% EtOAc in cyclohexane) gave 4-amino-N-isobutyl-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide (1.53 g, 98%). 1H NMR (300 MHz, CDCl3) δ 7.72 (dd, J=7.5, 2.1 Hz, 1H), 7.54-7.39 (m, 4H), 7.14 (d, J=7.7 Hz, 1H), 6.70-6.63 (m, 2H), 3.35 (dd, J=13.5, 8.3 Hz, 1H), 3.15 (dd, J=13.5, 5.3 Hz, 1H), 1.71-1.55 (m, 1H), 0.88 (d, J=6.5 Hz, 3H), 0.77 (d, J=6.7 Hz, 3H). LCMS (m/z, Method A) ES+ 373.1 [M+1]+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. filtrationThe cooled mixture was filtered through diatomaceous earth
  4. washwashing the filter cake with EtOH
  5. concentrationthe filtrate concentrated to low volume under vacuum
  6. customThe residue obtained
  7. extractionextracted into DCM
  8. dry with materialThe combined extracts were dried over Na2SO4
  9. concentrationconcentrated under vacuum
  10. customPurification by silica gel column chromatography (0-75% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-988bd929c2364284b32240d175d5c67a
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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