Ethylamine → HCID 21910576, compound

HRID 747390Notes

Reaction equation

HRID 747390 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.Br[N:19]1C(=O)C[CH2:21][C:20]1=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]([C:8]2[S:12](=[O:14])(=[O:13])[NH:11][C:10]([CH3:16])([CH3:15])[C:9]=2[CH2:17][NH:19][CH2:20][CH3:21])=[CH:6][CH:7]=1

Participants

8

Reactant 4

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

Product 1

HCID 21910576HCID 21910576, compoundYield 12%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 5-(4-chlorophenyl)-3,3,4-trimethyl-1,1-dioxo-2,3-dihydro-isothiazole, 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-methylpropionitrile). The mixture was heated to reflux for 4 h and 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 title amine 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-0c90a7d363da41b5bd4afd8c63038c97
Source dataset
uspto-grants-2008_07
Patent number
US07396846B2

Reaction notes

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