Hydrochloric Acid → HCID 57152078, compound

HRID 1635713Notes

Reaction equation

HRID 1635713 reaction equation
COC1C=C([S:9](Cl)(=[O:11])=[O:10])C=CC=1.[CH3:13][C:14]1[CH:15]=[C:16]([CH:18]=[C:19]([CH3:28])[C:20]=1[S:21]([CH2:24][N+:25]([O-:27])=[O:26])(=[O:23])=[O:22])[NH2:17].N1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl.O1CC[CH2:38][CH2:37]1>O>[CH3:28][C:19]1[CH:18]=[C:16]([NH:17][S:9]([CH2:30][CH:31]2[CH2:38][CH2:37][CH2:34][CH2:33][CH2:32]2)(=[O:11])=[O:10])[CH:15]=[C:14]([CH3:13])[C:20]=1[S:21]([CH2:24][N+:25]([O-:27])=[O:26])(=[O:22])=[O:23]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 8028TetrahydrofuranHCID 195716Ici 222155HCID 27375043-Methoxybenzenesulfonyl chloride

Product 1

HCID 57152078HCID 57152078, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-20 °C

Procedure

3.2 g (16.1 mmol) of cyclohexylmethanesulphonyl chloride (prepared according to J. F. King et al., J. Am. Chem. Soc., 1992, 114 (5), 1743) are added dropwise to a mixture, cooled to −20° C. and under a nitrogen atmosphere, of 2 g (8.18 mmol) of 3,5-dimethyl-4-[(nitromethyl)sulphonyl]aniline, 50 ml of anhydrous tetrahydrofuran and 1.3 ml (16.1 mmol) of pyridine, and the resulting mixture is stirred for 6 hours at −20° C. The mixture is left overnight at −20° C., it is then allowed to warm to room temperature and is stirred for 24 hours at room temperature and then refluxed for 13 hours. The mixture is cooled, poured into water, acidified to pH=3 with 1N HCl, extracted with CH2Cl2, washed with water, dried over Na2SO4, filtered and evaporated under vacuum. The residue is purified by chromatography on silica, eluting with CH2Cl2, and then recrystallized from a hexane/ethyl acetate mixture.

Workup

  1. waitThe mixture is left overnight at −20° C.
  2. temperatureto warm to room temperature
  3. stirringis stirred for 24 hours at room temperature
  4. temperaturerefluxed for 13 hours
  5. temperatureThe mixture is cooled
  6. extractionextracted with CH2Cl2
  7. washwashed with water
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated under vacuum
  11. customThe residue is purified by chromatography on silica
  12. washeluting with CH2Cl2
  13. customrecrystallized from a hexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-b4c9b4a27ad04e91ac1d75358c95c5ac
Source dataset
uspto-grants-2003_01
Patent number
US06509499B1

Reaction notes

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