Anthranilic Acid → 3-(3-Isopropoxy-phenyl)-2-thioxo-2,3-dihydro-1H-quinazolin-4-one

HRID 1292074Notes

Reaction equation

HRID 1292074 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([N:11]=[C:12]=[S:13])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].[C:14](O)(=[O:22])[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[NH2:17]>C(O)(=O)C>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([N:11]2[C:14](=[O:22])[C:15]3[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:17][C:12]2=[S:13])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 227Anthranilic AcidHCID 153811183-Isopropoxyphenyl isothiocyanate

Product 1

HCID 108289213-(3-Isopropoxy-phenyl)-2-thioxo-2,3-dihydro-1H-quinazolin-4-oneYield 72.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-isopropoxy aniline (6.0 g, 40 mmol), in 150 mL of CHC3 was added dropwise thiophosgene (2.81 mL, 44 mmol) at 0° C. After the addition of thiophosgene, triethylamine (7.0 mL, 48 mmol) was added slowly and the reaction mixture was stirred for 2 hours at room temperature. It was then concentrated and diluted with 200 mL of ethyl acetate. The triethylamine hydrochloride salt was filtered off and the filtrate was concentrated to yield crude 3-isopropoxyphenyl isothiocyanate. The crude 3-isopropoxyphenyl isothiocyanate was dissolved in 150 mL of acetic acid, and anthranilic acid (6.04 g, 44 mmol) was added. The resulting reaction mixture was refluxed for 16 hours and then cooled to room temperature. The white solid was separated which was filtered to yield 9.0 g of the title compound (72.1%), mp 288°-290° C.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 16 hours
  3. customThe white solid was separated which
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-ae6f381e8afc46f0a1904e5a0984003c
Source dataset
uspto-grants-1998_05
Patent number
US05756502

Reaction notes

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