Ethylenediamine → HCID 58641525, compound

HRID 2224063Notes

Reaction equation

HRID 2224063 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:18])[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.[CH2:24](N)[CH2:25][NH2:26]>C(Cl)(Cl)Cl.C(O)C>[C:1]1([S:7]([C:10]2[CH:23]=[CH:22][C:13]3[N:14]([CH2:19][C:20]4[NH:26][CH2:25][CH2:24][N:21]=4)[C:15](=[O:18])[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

5

Reactant 2

HCID 3301EthylenediamineHCID 58641512HCID 58641512, compound

Product 1

HCID 58641525HCID 58641525, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6212ChloroformSolvent2×

Conditions

Temperature
-15 °C

Procedure

To a solution of (7-benzenesulfonyl-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-acetonitrile (0.156 g., 0.475 mmol) in 10 mL anhydrous chloroform was added ethanol (0.029 mL, 0.5 mmol), and the resulting solution was cooled in a water ice/acetone bath to −15° C. Hydrogen chloride gas was bubbled through the solution for 10 minutes, and the flask was sealed and kept at −15° C. for 18 hours. The reaction mixture was concentrated in vacuo and 0.5 Torr vacuum was applied to the residue for 2 hours. The crude imidate was dissolved in 5 mL anhydrous chloroform, and to this solution was added ethylene diamine (0.033 mL, 0.5 mmol) in 4 mL anhydrous chloroform and 5 mL ethanol. The resulting solution was stirred at room temperature for 3 hours, and was then concentrated in vacuo. The residue was purified by flash chromatography (30% “magic base” (6:1:0.1 methylene chloride:methanol:ammonia) in dichlormethane) to give 0.130 g (0.35 mmol, 74%) of 7-benzenesulfonyl-4-(4,5-dihydro-1H-imidazol-2-ylmethyl)-4H-benzo[1,4]oxazin-3-one as a clear oil. MS: 372 (M+H)+, mp: 113.7-116.0° C. (HCl salt).

Workup

  1. customHydrogen chloride gas was bubbled through the solution for 10 minutes
  2. customthe flask was sealed
  3. concentrationThe reaction mixture was concentrated in vacuo and 0.5 Torr vacuum
  4. waitwas applied to the residue for 2 hours
  5. dissolutionThe crude imidate was dissolved in 5 mL anhydrous chloroform
  6. concentrationwas then concentrated in vacuo
  7. customThe residue was purified by flash chromatography (30% “magic base” (6:1:0.1 methylene chloride:methanol:ammonia) in dichlormethane)

Sources & evidence

ORD record
ord-3913fa6d81eb471ca06ef8ce55b89d69
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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