Tetrahydrofuran → HCID 12812389, compound

HRID 328129Notes

Reaction equation

HRID 328129 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][CH:26]=1)[NH:7][C:8]1[CH:23]=[CH:22][CH:21]=[CH:20][C:9]=1[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])([O-:3])=[O:2].[O:27]1CCC[CH2:28]1.[H-].[Na+].ClC1C=C(NC(N2C=CN=C2)=O)C=CC=1>O>[N+:1]([C:4]1[CH:5]=[C:6]([N:7]2[C:8]3[C:9](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:10](=[O:11])[N:12]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:28]2=[O:27])[CH:24]=[CH:25][CH:26]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 12394417HCID 12394417, compoundHCID 21444002HCID 21444002, compound

Product 1

HCID 12812389HCID 12812389, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3.5 g of 2-(m-nitroanilino)-N-benzylbenzamide and 30 ml of dry tetrahydrofuran was added 1.0 g of about 55 % sodium hydride, and stirring was performed for 30 minutes at room temperature. To this was added dropwise a solution of 4.9 g of 1-[N-(m-chlorophenyl)carbamoyl]imidazole and 30 ml of dry tetrahydrofuran. The mixture was allowed to stand for 30 minutes at room temperature and then refluxed for 2 hours. After the reaction was complete, the resulting mixture was filtered. The filtrate was concentrated under reduced pressure to leave a residue, to which was added water to precipitate a crude product. Recrystallization of this product from methanol gave 2.0 g of 1-(m-nitrophenyl)-3-benzylquinazoline-2,4(1H, 3H)-dione as colorless prisms, melting at 206°-207° C.

Workup

  1. waitto stand for 30 minutes at room temperature
  2. temperaturerefluxed for 2 hours
  3. filtrationthe resulting mixture was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto leave a residue
  6. customto precipitate a crude product
  7. customRecrystallization of this product from methanol

Sources & evidence

ORD record
ord-4b1cadfb2dcd4ff08b29cbf710070a02
Source dataset
uspto-grants-1977_04
Patent number
US04016166

Reaction notes

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