Formic Acid → HCID 710807, compound

HRID 726844Notes

Reaction equation

HRID 726844 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11](OC)(=[O:19])[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH2:14].C[O-].[Na+].C(O)=O>C1(C)C(C)=CC=CC=1.CO>[CH2:1]([N:8]1[C:11](=[O:19])[C:12]2[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:14][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 8635Methyl AnthranilateHCID 76639Benzyl isocyanateHCID 10942334Sodium Methoxide

Product 1

HCID 710807HCID 710807, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7237O-XyleneSolvent2×

Conditions

Temperature
110 °C

Procedure

A solution of benzyl isocyanate (13.3 g, 0.10 mol) in xylene (40 ml) is metered, at room temperature, into a solution of methyl anthranilate (15.1 g, 0.10 mol) in xylene (80 ml). After the addition has ended, the batch is stirred at 110° C. for 2 hours. 1.80 ml of a 30% solution of methanolic sodium methylate (0.010 ml) are metered in, and the mixture is stirred at 90° C. for a further 2 hours, during which process methanol is distilled off. 0.9 ml of 85% formic acid (0.020 mol) is subsequently added and the mixture is stirred at 90° C. for a further hour. After cooling, the product is filtered off with suction, washed with 3×25 ml of xylene, 3×25 ml of ethanol and 3×25 ml of water, and dried. 22.2 g of 3-(benzyl)-2,4(1H,3H)-quinazolinedione (yield: 88.0% of theory) of melting point 231° to 232° C. (lit. 227° to 228° C.) are obtained.

Workup

  1. additionAfter the addition
  2. stirringis stirred at 90° C. for a further 2 hours, during which
  3. distillationis distilled off
  4. stirringthe mixture is stirred at 90° C. for a further hour
  5. temperatureAfter cooling
  6. filtrationthe product is filtered off with suction
  7. washwashed with 3×25 ml of xylene, 3×25 ml of ethanol and 3×25 ml of water
  8. customdried

Sources & evidence

ORD record
ord-0f7aedbc89dd4bbb867d1eaa59e55a0c
Source dataset
uspto-grants-1998_01
Patent number
US05710319

Reaction notes

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