Phosphorus oxychloride → HCID 90410174, compound

HRID 589034Notes

Reaction equation

HRID 589034 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[C:16]3[O:15][CH2:14][CH:13]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:12]4[C:23](=O)[NH:24][C:10]([C:11]=34)=[CH:9][CH:8]=2)=[C:5]([CH3:26])[O:4][N:3]=1.P(Cl)(Cl)([Cl:29])=O>>[Cl:29][C:23]1[N:12]2[CH:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14][O:15][C:16]3=[C:11]2[C:10](=[CH:9][CH:8]=[C:7]3[C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[CH3:26])[N:24]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 90409629HCID 90409629, compound

Product 1

HCID 90410174HCID 90410174, compoundYield 100%

Conditions

Temperature
95 °C

Procedure

To 7-(3,5-dimethylisoxazol-4-yl)-4-phenyl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (40.0 mg, 0.115 mmol) in a vial, phosphoryl chloride (1.5 mL, 16 mmol) was added and the mixture was heated at 95° C. overnight. The mixture was evaporated and extracted with EtOAc. The extracts were washed with saturated sodium bicarbonate, brine and dried over sodium sulfate. Filtration and evaporation gave the desired compound (42 mg, 100%). LCMS calc. for C20H17ClN3O2 (M+H)+: m/z=366.1. found: 366.1.

Workup

  1. customThe mixture was evaporated
  2. extractionextracted with EtOAc
  3. washThe extracts were washed with saturated sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-4fc2a6137b67462ea7265850339065b0
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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