Benzylamine → HCID 54757216, compound

HRID 1782158Notes

Reaction equation

HRID 1782158 reaction equation
[CH3:1][C:2]1[C:6]2[N:7]=[C:8]([CH2:12][CH2:13][CH3:14])O[C:10](=[O:11])[C:5]=2[S:4][N:3]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>Cl>[CH2:15]([N:22]1[C:10](=[O:11])[C:5]2[S:4][N:3]=[C:2]([CH3:1])[C:6]=2[N:7]=[C:8]1[CH2:12][CH2:13][CH3:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 54757215HCID 54757215, compound

Product 1

HCID 54757216HCID 54757216, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
200 °C

Procedure

3-Methyl-5-propyl-isothiazolo[4,5-d][1,3]oxazin-7-one (method 58) (200 mg, 1.02 mmol) was taken in a 10 mL microwavable pyrex tube and benzyl amine (1 g, 9.34 mmol) was added to it. The resulting mixture was heated in a microwave synthesizer (CEM's Discoverer) at 200° C. for 20 min. The MS of the reaction mixture showed the complete disappearance of the starting material and the presence of the product peak at 286 (MH+). The reaction mixture was diluted with 1N HCl (10 mL) and extracted with EtOAc (2×30 mL). The combined EtOAc layers were washed with water, brine, dried and concentrated. The thus obtained crude product was purified by column chromatography to isolate the pure product as a white solid. Yield 208 mg (71%). 1H NMR (300 MHz) δ 0.98 (t, 3H), 1.76-1.88 (m, 2H), 2.68 (s, 3H), 2.74 (t, 2H), 5.42 (s, 2H), 7.10-7.19 (m, 2H), 7.28-7.39 (m, 3H).

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe combined EtOAc layers were washed with water, brine
  3. customdried
  4. concentrationconcentrated
  5. customThe thus obtained crude product
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6ff559a3b35b48078af70975912cd821
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

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