Dimethylformamide → HCID 12812379, compound

HRID 328133Notes

Reaction equation

HRID 328133 reaction equation
CO[C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1.CN(C)C=O.[NH2-].[Na+].[CH2:28]([N:31]=[C:32]=[O:33])[CH2:29][CH3:30]>O>[N+:17]([C:13]1[CH:12]=[C:11]([N:10]2[C:5]3[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:3](=[O:20])[N:31]([CH2:28][CH2:29][CH3:30])[C:32]2=[O:33])[CH:16]=[CH:15][CH:14]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24533Sodium amideHCID 61033Propyl isocyanateHCID 54146698HCID 54146698, compound

Product 1

HCID 12812379HCID 12812379, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.9 g of 2-(m-nitroanilino)benzoic acid methyl ester and 20ml of dry dimethylformamide was added 0.43 g of sodium amide, and the whole was stirred for 30 minutes. To this was added dropwise under cooling 2.6 g of propyl isocyanate. This mixture was allowed to stand for one hour at room temperature and for additional one hour at 60° C, and then reacted for 4 hours at 120° C. The solvent was distilled off from the mixture under reduced pressure. To the residue obtained was added water to precipitate a crude product. This product was recrystallized from methanol to produce 2.4 g of 1-(m-nitrophenyl)-3-propylquinazoline-2,4(1H, 3H)-dione as colorless needles, melting at 162°-163° C.

Workup

  1. additionTo this was added dropwise
  2. waitto stand for one hour at room temperature and for additional one hour at 60° C
  3. customreacted for 4 hours at 120° C
  4. distillationThe solvent was distilled off from the mixture under reduced pressure
  5. customTo the residue obtained
  6. customto precipitate a crude product
  7. customThis product was recrystallized from methanol

Sources & evidence

ORD record
ord-15d074c3df7a43b3884b97492d2478e2
Source dataset
uspto-grants-1977_04
Patent number
US04016166

Reaction notes

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