Water → HCID 12812387, compound

HRID 328130Notes

Reaction equation

HRID 328130 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[NH:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[C:10]([NH:12][CH2:13][CH2:14][O:15][CH2:16][CH3:17])=[O:11])([O-:3])=[O:2].[H-].[Na+].CN(C)[C:29](Cl)=[O:30].O>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([N:7]2[C:8]3[C:9](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:10](=[O:11])[N:12]([CH2:13][CH2:14][O:15][CH2:16][CH3:17])[C:29]2=[O:30])[CH:22]=[CH:23][CH:24]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 21444006HCID 21444006, compound

Product 1

HCID 12812387HCID 12812387, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.3 g of 2-(m-nitroanilino)-N-(2-ethoxyethyl)benzamide was dissolved in 30 ml of dry tetrahydrofuran, and to the solution was added 1.0 g of approximately 50 % sodium hydride. After stirring the mixture for 30 minutes, 3.2 g of N,N-dimethylcarbamoyl chloride was further added dropwise under cooling, and the whole was refluxed for 4 hours. After the reaction was complete, the solvent was evaporated 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 ethanol to give 3.1 g of 1-(m-nitrophenyl)-3-(2-ethoxyethyl)quinazoline-2,4(1H, 3H)-dione as pale yellow prisms, melting at 161°-162° C.

Workup

  1. temperatureunder cooling
  2. temperaturethe whole was refluxed for 4 hours
  3. customthe solvent was evaporated from the resulting mixture under reduced pressure
  4. customTo the residue thus obtained
  5. customto yield a crude product
  6. customThis product was recrystallized from ethanol

Sources & evidence

ORD record
ord-66bd11ae3d1a4f04be1fc38a5ffeb1d3
Source dataset
uspto-grants-1977_04
Patent number
US04016166

Reaction notes

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