Tetrahydrofuran → HCID 12812379, compound

HRID 328126Notes

Reaction equation

HRID 328126 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][CH2:14][CH3:15])=[O:11])([O-:3])=[O:2].[O:23]1CCC[CH2:24]1.[H-].[Na+].C(N1C=CN=C1)(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][CH2:14][CH3:15])[C:24]2=[O:23])[CH:20]=[CH:21][CH:22]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 21444005HCID 21444005, compound

Product 1

HCID 12812379HCID 12812379, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3.0 g of 2-(m-nitroanilino)-N-propylbenzamide and 50 ml of tetrahydrofuran were added 1.1 g of 50 % sodium hydride and 4.9 g of 1,1' -carbonyldiimidazole. The mixture was stirred for one hour at room temperature and then refluxed for 5 hours. After the reaction was finished, the solvent was distilled off from the resulting mixture under reduced pressure, and to the residue obtained was added water to yield a precipitate. This product was recrystallized from methanol to yield 2.6 g of 1-(m-nitrophenyl)-3 -propylquinazoline-2,4(1H, 3H)-dione as colorless prisms, melting at 162°-163° C.

Workup

  1. temperaturerefluxed for 5 hours
  2. distillationthe solvent was distilled off from the resulting mixture under reduced pressure
  3. customto the residue obtained
  4. customto yield a precipitate
  5. customThis product was recrystallized from methanol

Sources & evidence

ORD record
ord-ee32fef3bce64dda93d125428a282a20
Source dataset
uspto-grants-1977_04
Patent number
US04016166

Reaction notes

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