HCID 58641512, compound → HCID 58641559, compound

HRID 2224064Notes

Reaction equation

HRID 2224064 reaction equation
[C:1]1([S:7]([C:10]2[CH:23]=[CH:22][C:13]3[N:14]([CH2:19][C:20]#[N:21])[C:15](=O)[CH2:16][O:17][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1>[C:1]1([S:7]([C:10]2[CH:23]=[CH:22][C:13]3[N:14]([CH2:19][CH2:20][NH2:21])[CH2:15][CH2:16][O:17][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 58641512HCID 58641512, compound

Product 1

HCID 58641559HCID 58641559, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (7-benzenesulfonyl-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-acetonitrile (0.234 g., 0.713 mmol) in 2 mL anhydrous THF was warmed to reflux, and borane-methyl sulfide complex (0.5 mL of a 10 M solution, 5 mmol) was added dropwise over 5 minutes. Reflux was continued for 4 hours, and the reaction mixture was concentrated in vacuo. The residue was then dissolved in 2 mL ethanol and ethanolic hydrogen chloride was added (2 mL of a 2 N solution, 4 mmol.) The solution was refluxed for 18 hours then cooled to room temperature, resulting in formation of a precipitate. The solid was filtered and dried under vacuum for 18 hours to give 0.158 g (0.496 mmol, 70%) of 2-(7-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-ethylamine as a yellowish solid. MS: 319 (M+H)+, mp: 261.0-265.1° C. (HCl salt).

Workup

  1. temperatureto reflux
  2. temperatureReflux
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. dissolutionThe residue was then dissolved in 2 mL ethanol
  5. additionethanolic hydrogen chloride was added (2 mL of a 2 N solution, 4 mmol
  6. temperature) The solution was refluxed for 18 hours
  7. customresulting in formation of a precipitate
  8. filtrationThe solid was filtered
  9. customdried under vacuum for 18 hours

Sources & evidence

ORD record
ord-4884394970e94b3c984d3f51fa30ea3c
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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