Imidazole → HCID 15187963, compound

HRID 2195748Notes

Reaction equation

HRID 2195748 reaction equation
[H-].[Na+].CN(C)C=O.[NH:8]1[CH:12]=[CH:11][N:10]=[CH:9]1.[Cl:13][C:14]1[N:23]=[C:22](Cl)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1>O1CCCC1>[Cl:13][C:14]1[N:23]=[C:22]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 2528862,4-Dichloroquinazoline

Product 1

HCID 15187963HCID 15187963, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 60% sodium hydride (426 mg) in tetrahydrofuran (4 mL)-N,N-dimethylformamide (24 mL) was added imidazole (725 mg), and the mixture was stirred at room temperature for 30 minutes. To the mixture was added dropwise a tetrahydrofuran solution (35 mL) of 2,4-dichloroquinazoline (2.12 g) synthesized according to the method of H. C. Scarborough et al. (Journal of Organic Chemistry, 1962, pp. 957-961), in ice-acetone bath, and the mixture was stirred for 30 minutes. The reaction mixture was poured into ice-cold water, and precipitated powder was collected by filtration, washed with water and dried. The obtained powder was purified by silica gel column chromatography, (ethyl acetate), to give 1.88 g of 2-chloro-4-(1-imidazolyl)-quinazoline as colorless crystals (yield 77%).

Workup

  1. customsynthesized
  2. additionThe reaction mixture was poured into ice-cold water
  3. customprecipitated powder
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried
  7. customThe obtained powder was purified by silica gel column chromatography, (ethyl acetate),

Sources & evidence

ORD record
ord-5332fe1514074b0eb674685fb5b6147d
Source dataset
uspto-grants-2012_12
Patent number
US08338420B1

Reaction notes

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