Phosphorus oxychloride → HCID 59145634, compound

HRID 1842583Notes

Reaction equation

HRID 1842583 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=O)[C:5]2[CH2:10][CH:9]([CH3:11])[CH2:8][C:6]=2[N:7]=1.P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:4]1[C:5]2[CH2:10][CH:9]([CH3:11])[CH2:8][C:6]=2[N:7]=[C:2]([NH2:1])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135741896HCID 135741896, compound

Product 1

HCID 59145634HCID 59145634, compoundYield 34%

Procedure

Compound 2 (297 mg, 1.8 mmol) and phosphorus oxychloride (15 mL) were heated to reflux for 3 h. The reaction mixture was cooled and evaporated at reduced pressure, and the residue was diluted with chloroform (50 mL) and neutralized with ammonium hydroxide slowly in an ice bath. The organic portion was washed with water (3×30 mL). Solvents were evaporated at reduced pressure, and the residue was purified by column chromatography using chloroform/hexane (4/1) as eluent to afford 112 mg (34%) of 3 as a white-off solid TLC Rf0.48 (CHCl3/CH3OH, 10:1); mp: 181.5-182.9° C., 1H NMR (DMSO-6): δ 1.16-1.18 (d, 3 H, CH3), δ 1.55-1.65, 2.15-2.38, 2.49-2.62, 2.83-2.92 (m, 5 H, CH2CHCH2), δ 6.83 (br, 2H, NH2, exch). Anal. (C8H10ClN3) C, H, N, Cl: calcd, 52.32, 5.49, 22.88, 19.31; found, 52.33, 5.62, 22.63, 19.09.

Workup

  1. temperatureto reflux for 3 h
  2. temperatureThe reaction mixture was cooled
  3. customevaporated at reduced pressure
  4. additionthe residue was diluted with chloroform (50 mL)
  5. customneutralized with ammonium hydroxide slowly in an ice bath
  6. washThe organic portion was washed with water (3×30 mL)
  7. customSolvents were evaporated at reduced pressure
  8. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-94b3cdd5180346c2bd4072dd7bd9acfc
Source dataset
uspto-grants-2015_02
Patent number
US08946239B2

Reaction notes

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