1,3-Dimethyl-2-imidazolidinone → HCID 54459706, compound

HRID 1250612Notes

Reaction equation

HRID 1250612 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=O)[NH:8][C:7]2=O)([O-:3])=[O:2].CN1CCN(C)C1=O.P(Cl)(Cl)(Cl)=O.C(N(CC)CC)C.[ClH:36].[CH3:37][CH:38]([NH2:41])[CH:39]=[CH2:40]>O>[Cl:36][C:9]1[N:8]=[C:7]([NH:41][CH:38]([CH3:37])[CH:39]=[CH2:40])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1

Participants

7

Reactant 5

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedioneHCID 18185425BUT-3-EN-2-AMINE HCL

Product 1

HCID 54459706HCID 54459706, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 278 mg (1.45 mmol) of 6-nitroquinazoline-2,4(1H,3H)-dione were added 0.71 ml of 1,3-dimethyl-2-imidazolidinone and 5.48 g (35.76 mmol) of phosphorus oxychloride, and the resulting mixture was subjected to heating under reflux for 3 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 3 ml of acetonitrile, followed by addition of 2.81 ml (20.07 mmol) of triethylamine and 281 mg (2.61 mmol) of 1-methyl-2-propenylamine hydrochloride and stirring under ice cooling for 2 hours. To the reaction solution was added water, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off to give 2-chloro-4-(1-methyl-2-propenylamino)-6-nitroquinazoline. After 1.00 ml (10.12 mmol) of n-butylamine was added thereto and then the mixture was stirred at room temperature for 3 hours, water was added to the reaction solution, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 73 mg (17.3%) of the title compound.

Workup

  1. temperatureto heating
  2. temperatureunder reflux for 3 hours
  3. customAfter phosphorus oxychloride was removed in vacuo
  4. dissolutionthe mixture was dissolved in 3 ml of acetonitrile
  5. extractionfollowed by extraction with ethyl acetate
  6. washwashing with brine
  7. dry with materialdrying over anhydrous sodium sulfate
  8. distillationAfter the solvent was distilled off

Sources & evidence

ORD record
ord-ae2cc88b4ba04e1c91dcbef892969cc1
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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