2-Tolyl isocyanate → HCID 15295490, compound

HRID 1735965Notes

Reaction equation

HRID 1735965 reaction equation
[C:1]1([CH3:10])[C:2]([N:7]=[C:8]=[O:9])=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([NH2:25])[C:16](=[CH:21][C:22]=1[O:23][CH3:24])[C:17](OC)=[O:18].C[O-].[Na+]>C1(C)C=CC=CC=1>[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:17](=[O:18])[C:16]2[C:15](=[CH:14][C:13]([O:12][CH3:11])=[C:22]([O:23][CH3:24])[CH:21]=2)[NH:25][C:8]1=[O:9]

Participants

5

Reactant 3

HCID 691942-Tolyl isocyanateHCID 611144Methyl 4,5-dimethoxyanthranilateHCID 10942334Sodium Methoxide

Product 1

HCID 15295490HCID 15295490, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

A solution of o-tolyl isocyanate (13.3 g, 0.10 mol) in toluene (40 ml) is metered at room temperature into a solution of methyl 4,5-dimethoxyanthranilate (21.1 g, 0.10 mol) in toluene (70 ml). After addition is complete, the mixture is stirred at 90° C. for 2 hours. 1.80 ml of a 30% strength solution of methanolic sodium methoxide (0.010 mol) are metered in and the mixture is stirred at 90° C. for a further 1 hour, methanol being distilled off. After cooling, the product is filtered off with suction and washed with 3×30 ml of toluene. The toluene-moist precipitate is treated with dilute sulfuric acid and the residual toluene is removed by azeotropic distillation. The product is then filtered off with suction, washed with water and dried. 29.0 g of 3-(2-tolyl)-6,7-dimethoxy-2,4(1H,3H)-quinazolinedione (yield: 92.9% of theory) of melting point 282° to 284° C. are obtained.

Workup

  1. additionAfter addition
  2. stirringis stirred at 90° C. for a further 1 hour
  3. distillationmethanol being distilled off
  4. temperatureAfter cooling
  5. filtrationthe product is filtered off with suction
  6. washwashed with 3×30 ml of toluene
  7. additionThe toluene-moist precipitate is treated with dilute sulfuric acid
  8. customthe residual toluene is removed by azeotropic distillation
  9. filtrationThe product is then filtered off with suction
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-ba22f885a79848c9af3f0a71ef26a53b
Source dataset
uspto-grants-1996_07
Patent number
US05539114

Reaction notes

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