Tetrahydrofuran → HCID 12812382, compound

HRID 328127Notes

Reaction equation

HRID 328127 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[NH:7][C:8]1[CH:19]=[CH:18][CH:17]=[CH:16][C:9]=1[C:10]([NH:12][CH2:13][C:14]#[CH:15])=[O:11])([O-:3])=[O:2].[O:23]1CCC[CH2:24]1.[H-].[Na+].ClC(Cl)(Cl)C(N1C=CN=C1)=O>O>[N+:1]([C:4]1[CH:5]=[C:6]([N:7]2[C:8]3[C:9](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:10](=[O:11])[N:12]([CH2:13][C:14]#[CH:15])[C:24]2=[O:23])[CH:20]=[CH:21][CH:22]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 565237HCID 565237, compoundHCID 21444003HCID 21444003, compound

Product 1

HCID 12812382HCID 12812382, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3.0 g of 2-(m-nitroanilino)-N-propargylbenzamide and 25 ml of dry tetrahydrofuran was added 1.0 g of approximately 55 % sodium hydride, and the solution was stirred for 30 minutes at room temperature. To this was added dropwise 2.1 g of 1-trichloroacetylimidazole and the mixture was refluxed for one hour. After the reaction was complete, the solvent was distilled off from the resulting mixture under reduced pressure. To the residue thus obtained was added water to yield a crude product. This product was recrystallized from methanol to yield 2.8 g of 1-(m-nitrophenyl) -3-propargylquinazoline-2,4(1H, 3H)-dione as colorless needles, melting at 222°-223° C.

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. distillationthe solvent was distilled off from the resulting mixture under reduced pressure
  3. customTo the residue thus obtained
  4. customto yield a crude product
  5. customThis product was recrystallized from methanol

Sources & evidence

ORD record
ord-aab2282df4fb486fb4f8e0eb60ac6d4d
Source dataset
uspto-grants-1977_04
Patent number
US04016166

Reaction notes

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