Water → HCID 118251575, compound

HRID 2203180Notes

Reaction equation

HRID 2203180 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][C:12]([NH:14][CH2:15][C:16]3[CH:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][N:17]=3)=O)[CH:10]=1)[N:7]([CH2:26][CH:27]([CH3:29])[CH3:28])[N:6]=[CH:5]2.P(Cl)(Cl)(Cl)=O.O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][C:12]3[N:17]4[CH:18]=[CH:19][C:20]([C:22]([O:24][CH3:25])=[O:23])=[CH:21][C:16]4=[CH:15][N:14]=3)[CH:10]=1)[N:7]([CH2:26][CH:27]([CH3:29])[CH3:28])[N:6]=[CH:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 118251619HCID 118251619, compound

Product 1

HCID 118251575HCID 118251575, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A solution/suspension of compound 59 (0.184 g, 0.44 mmol) in toluene was treated with phosphorus oxychloride (1 ml) and stirred at 90° C. under a nitrogen atmosphere for 22.5 h. The mixture was cooled and treated with water (20 ml) then neutralised by addition of solid sodium hydrogen carbonate. The mixture was then extracted with ethyl acetate (2×25 ml) and the organics separated and dried over sodium sulphate, filtered and evaporated to dryness. The residue was chromatographed on silica gel eluting with an ethyl acetate/isohexane gradient to give the title compound as a yellow oil (0.092 g, 52%).

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was then extracted with ethyl acetate (2×25 ml)
  3. customthe organics separated
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was chromatographed on silica gel eluting with an ethyl acetate/isohexane gradient

Sources & evidence

ORD record
ord-639afee81cd4467897239d2f2d9eb6b1
Source dataset
uspto-grants-2016_06
Patent number
US09365569B2

Reaction notes

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