4-Chlorophenyl Isocyanate → HCID 3958937, compound

HRID 1735962Notes

Reaction equation

HRID 1735962 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[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+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:19])[C:12]3[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:14][C:9]2=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 8635Methyl AnthranilateHCID 10942334Sodium Methoxide

Product 1

HCID 3958937HCID 3958937, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

A solution of p-chlorophenyl isocyanate (15.3 g, 0.10 mol) in toluene (50 ml) is metered at room temperature into a solution of methyl anthranilate (15.1 g, 0.10 mol) in toluene (100 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 3×20 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. 26.8 g of 3-(4-chlorophenyl)-2,4(1H,3H)-quinazolinedione (yield: 98.3% of theory) of melting point 290° to 292° 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 3×20 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-8da19d9f1dd444cf970c1bca498aa34b
Source dataset
uspto-grants-1996_07
Patent number
US05539114

Reaction notes

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