Phosphorus oxychloride → HCID 11820387, compound

HRID 718112Notes

Reaction equation

HRID 718112 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=O)[NH:5][CH2:4][C:3]1=[O:14].P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:2]([CH3:1])[C:3](=[O:14])[CH2:4][N:5]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 35623871-Methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione

Product 1

HCID 11820387HCID 11820387, compound

Procedure

The title compound 467 (1.54 g, 8.10 mmol) was heated in phosphorus oxychloride (15 mL) at 95° C. for 2 hours. The reaction mixture was then cooled to room temperature and excess of phosphorus oxychloride was removed under reduced pressure. The black oil was dissolved in ethyl acetate and the organic phase was washed with sodium bicarbonate (saturated solution) and brine, dried over sodium sulfate, filtered and concentrated to afford crude title compound 468 that was used as such for the next step. MS (ESI): 209.12 (MH)+.

Workup

  1. customwas removed under reduced pressure
  2. dissolutionThe black oil was dissolved in ethyl acetate
  3. washthe organic phase was washed with sodium bicarbonate (saturated solution) and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-00498f7125bb4c3fb25e41046bac7fb5
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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