Ethylamine → HCID 21910631, compound

HRID 1245288Notes

Reaction equation

HRID 1245288 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12](=[O:14])(=[O:13])[NH:11][C:10]([CH3:16])([CH3:15])[C:9]=2[CH3:17])=[CH:4][CH:3]=1.BrN1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C(N)C>C(Cl)(Cl)(Cl)Cl.C(O)C.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][S:12]([NH:11][C:10]([CH3:16])([CH3:15])[C:9]#[CH:17])(=[O:14])=[O:13])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 6341EthylamineHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 21910673HCID 21910673, compound

Product 1

HCID 21910631HCID 21910631, compoundYield 12%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 5-(4-Chloro-phenyl)-3,3,4-trimethyl-2,3-dihydro-isothiazole 1,1-dioxide, 1.5 g (5.5 mmol) in 150 mL of carbon tetrachloride was added 1.5 g (8.25 mmol) of N-bromosuccinimide and 0.13 g of 2,2′-azobis(2-methyl-propionitrile). The mixture was heated to reflux for 4 h then cooled to ambient temperature. Chloroform was added and the solution was washed with water, washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. To a solution of the residue in 75 mL of absolute ethanol was added 3.6 mL (55.0 mmol) of ethylamine (70% solution in water). The reaction mixture was stirred 24 h at ambient temperature then concentrated to dryness. The residue was purified by chromatography on silica gel with methanol/chloroform as eluant to yield 0.21 g (12%) of the desired product, shown below, as a tan oil. 1H-NMR is consistent with structure; MS (ion spray) 313.0 (M−1); Anal. Calc'd for C14H19ClN2O2S.0.1CHCl3: C, 51.83; H, 5.89; N, 8.57. Found: C, 51.58; H, 6.38; N, 8.04.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 h
  3. washthe solution was washed with water
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. concentrationthen concentrated to dryness
  9. customThe residue was purified by chromatography on silica gel with methanol/chloroform as eluant

Sources & evidence

ORD record
ord-0e4acec30ed14920bc4524c547b6cae3
Source dataset
uspto-grants-2006_10
Patent number
US07125840B2

Reaction notes

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