O-Xylene → HCID 15295489, compound

HRID 1735964Notes

Reaction equation

HRID 1735964 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]=[C:8]=[O:9])[CH:2]=1.[F:11]C1C=C(N)C(=CC=1)C(OCC)=O.[OH-:24].C([N+:29]([CH2:38]CCC)([CH2:34][CH2:35][CH2:36][CH3:37])CCCC)CCC.[C:42]1([CH3:49])C(C)=CC=CC=1>>[F:11][C:37]1[CH:42]=[C:49]2[C:34](=[CH:35][CH:36]=1)[NH:29][C:38](=[O:24])[N:7]([C:3]1[CH:2]=[C:1]([CH3:10])[CH:6]=[CH:5][CH:4]=1)[C:8]2=[O:9]

Participants

5

Reactant 4

HCID 7237O-Xylene2×HCID 69303m-Tolyl isocyanateHCID 2723671Tetrabutylammonium HydroxideHCID 14233600Ethyl 2-Amino-4-fluorobenzoate

Product 1

HCID 15295489HCID 15295489, compoundYield 91.7%

Conditions

Temperature
90 °C

Procedure

A solution of m-tolyl isocyanate (33.3 g, 0.25 mol) in xylene (100 ml) is metered at room temperature into a solution of ethyl 4-fluoroanthranilate (45.8 g, 0.25 mol) in xylene (250 ml). After addition is complete, the mixture is stirred at 90° C. for 2.5 hours. 32.5 ml of a 20% strength solution of aqueous tetrabutylammonium hydroxide (0.025 mol) are metered in and the mixture is stirred at 90° C. for a further 2 hours, ethanol being distilled off. After cooling, the product is filtered off with suction and washed with 3×30 ml of xylene. The xylene-moist precipitate is treated with dilute hydrochloric acid and the residual xylene is removed by azeotropic distillation. The product is then filtered off with suction, washed with water and dried. 62.0 g of 6-fluoro-3-(3-tolyl)-2,4(1H,3H)-quinazolinedione (yield: 91.7% of theory) of melting point 278° to 279° C. are obtained.

Workup

  1. additionAfter addition
  2. stirringis stirred at 90° C. for a further 2 hours
  3. distillationethanol being distilled off
  4. temperatureAfter cooling
  5. filtrationthe product is filtered off with suction
  6. washwashed with 3×30 ml of xylene
  7. additionThe xylene-moist precipitate is treated with dilute hydrochloric acid
  8. customthe residual xylene 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-ea0450a7f80e42379239d969152d9937
Source dataset
uspto-grants-1996_07
Patent number
US05539114

Reaction notes

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