Ammonia → HCID 77230828, compound

HRID 921038Notes

Reaction equation

HRID 921038 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][NH:16][C:15]2=O)([CH3:9])([CH3:8])[CH3:7].N>C1(C)C=CC=CC=1.CN(C)C1C=CC=CC=1>[Cl:3][C:15]1[C:14]2[C:19](=[C:10]([C:6]([CH3:9])([CH3:8])[CH3:7])[CH:11]=[CH:12][CH:13]=2)[N:18]=[CH:17][N:16]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 136278287HCID 136278287, compound

Product 1

HCID 77230828HCID 77230828, compound

Reagents, catalysts & solvents 2

HCID 949N,N-DimethylanilineCatalystHCID 1140TolueneSolvent2×

Procedure

18.6 ml (200 mmol) of phosphoryl chloride are added dropwise at room temperature to a suspension of 10.2 g (50 mmol) of 8-tert-butyl-4(3H)-quinazolinone in 100 ml of toluene. After addition of 5 drops of N,N-dimethylaniline, the reaction mixture is heated under reflux for 5 h. After cooling, the reaction mixture is diluted with 300 ml of toluene, poured onto 1000 g of ice and rendered alkaline (pH about 9) by addition of conc. ammonia solution. The organic phase is separated off, washed once with 300 ml of sat. sodium chloride solution, dried over magnesium sulfat e, and the toluene is removed in vacuo. The residue is chromatographed on silica gel (n-heptane:ethyl acetate 3:1 v:v). Yield: 9.3 g (42 mmol), 84%. Purity: >95% according to 1H-NMR.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 5 h
  3. temperatureAfter cooling
  4. customThe organic phase is separated off
  5. washwashed once with 300 ml of sat. sodium chloride solution
  6. dry with materialdried over magnesium sulfat e
  7. customthe toluene is removed in vacuo
  8. customThe residue is chromatographed on silica gel (n-heptane:ethyl acetate 3:1 v:v)

Sources & evidence

ORD record
ord-f31949a0913843b58d7b5ba35f99528f
Source dataset
uspto-grants-2016_03
Patent number
US09273080B2

Reaction notes

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