Hydrochloric Acid → HCID 15933912, compound

HRID 44437Notes

Reaction equation

HRID 44437 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.Cl.[I-:19].[Na+].C(#N)C>C1COCC1.CCOCC>[I:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 6342AcetonitrileHCID 809774-Chloro-2-phenylquinazoline

Product 1

HCID 15933912HCID 15933912, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the 4-chloro-2-phenylquinazoline (4.15 mmol) in dry THF (10 ml) was added a solution of 2 M HCl in ether (4 ml). After 5 min the solvents were removed by vacuum. Dry sodium iodide (41.5 mmol) and acetonitrile (30 ml) were added to the hydrochloride salt and refluxed for 4 hrs. The reaction was quenched by the addition of an aqueous solution of 10% K2CO3 and 5% NaHSO3 (15 ml). Extraction with dichloromethane and drying of the combined organic layers was followed by evaporation of solvents under reduced pressure. The resulting crude product was purified by alumina chromatography with (1:10)

Workup

  1. customAfter 5 min the solvents were removed by vacuum
  2. temperaturerefluxed for 4 hrs
  3. customThe reaction was quenched by the addition of an aqueous solution of 10% K2CO3 and 5% NaHSO3 (15 ml)
  4. extractionExtraction with dichloromethane
  5. customdrying of the combined organic layers
  6. customwas followed by evaporation of solvents under reduced pressure
  7. customThe resulting crude product was purified by alumina chromatography with (1:10)

Sources & evidence

ORD record
ord-b9df016134b34f5ba34697fd40377583
Source dataset
uspto-grants-2013_09
Patent number
US08541428B2

Reaction notes

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