4-Chlorophenyl Isocyanate → HCID 21242496, compound

HRID 569000Notes

Reaction equation

HRID 569000 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[I:11][C:12]1[CH:20]=[C:16]([C:17]([OH:19])=[O:18])[C:15]([NH2:21])=[CH:14][CH:13]=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:21][C:15]2[CH:14]=[CH:13][C:12]([I:11])=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 72911Benzoic acid, 2-amino-5-iodo-

Product 1

HCID 21242496HCID 21242496, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2-(4-Chlorophenylaminocarbonylamino)-5-iodobenzoic acid was prepared by adding a solution of 4-chlorophenyl isocyanate (15.4 g) in ethyl acetate (60 ml) dropwise, at room temperature, to a stirred suspension of 5-iodoanthranilic acid (26.3 g) in ethyl acetate (150 ml). The mixture was heated at reflux for 1 hour, cooled to ambient temperature and the solid removed by filtration, to give 34 g of the substituted benzoic acid. This (34 g) was added to absolute alcohol (250 ml) saturated with hydrogen chloride gas and heated at reflux for 40 minutes. When cool, the solid was filtered and washed with absolute alcohol (50 ml) to give 27.1 g of 3-(4-chlorophenyl)-6-iodoquinazoline-2,4(1H,3H)-dione, mp 324°-6° C. This product (26.9 g) was added slowly to a mixture of pyridine (25 ml) and phosphoryl chloride (250 ml). The mixture was heated at reflux for 6 hours, when a solution developed. When cool, excess phosphoryl chloride and pyridine were removed by distillation in vacuo. The residue was cautiously added to ice water (500 ml) and the solid filtered. This solid was extracted with dichloromethane (100 ml), the extract concentrated in vacuo and chromatographed on silica using dichloromethane to give 9.7 g of 2-chloro-3-(4-chlorophenyl)-6-iodoquinazolin-4(3H)-one, mp 178°-180° C. This was then treated with 1,2,4-triazole and potassium carbonate in a similar manner to Example 1 to give 3-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-6-iodoquinazolin-4(3H)-one, mp 206°-208° C. (Compound 2).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customthe solid removed by filtration

Sources & evidence

ORD record
ord-aa42a94865a34745b0e3fc3795a03ce3
Source dataset
uspto-grants-1988_03
Patent number
US04731106

Reaction notes

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