Anthranilic Acid → HCID 178481666, compound

HRID 371623Notes

Reaction equation

HRID 371623 reaction equation
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH3:11][N:12]=[C:13]=[S:14]>C(O)C>[SH:14][C:13]1[N:12]([CH3:11])[C:1](=[O:10])[C:2]2[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:4]=1

Participants

4

Reactant 2

HCID 227Anthranilic AcidHCID 11167Methyl isothiocyanate

Product 1

HCID 178481666HCID 178481666, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of anthranilic acid (22.5 g), methyl isothiocyanate (12.5 g) and ethanol (200 ml) was refluxed for 3 hours, cooled and the precipitate filtered off and washed with water. Recrystallisation from ethanol gave 2-mercapto-3-methyl-3,4-dihydroquinazolin-4-one (13.0 g, m.p. 265°-266°). A mixture of this material (5.76 g) hydrazine hydrate (20 ml) and ethanol (30 ml) was refluxed for 30 minutes, then cooled. The precipitate was filtered off, washed with water and dried to give the 2-hydrazinoquinazolinone (3.16 g, m.p. 220°-223°). Recrystallisation from ethanol gave material m.p. 223°. A stirred solution of the crude product (1.9 g) in a mixture of hydrochloric acid (20 ml, 2N) and acetic acid (10 ml) was treated dropwise at 0°-5° with a solution of sodium nitrite (0.69 g) in water (5 ml). The mixture was allowed to attain room temperature and, after 1 hour, was filtered and the precipitate washed with water and dried to give the title compound (1.04 g., m.p. 164°-167°). Recrystallisation from ethanol gave material m.p. 167°.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperaturecooled
  3. filtrationthe precipitate filtered off
  4. washwashed with water
  5. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-6e540baa91684a48b353d344d0328ebd
Source dataset
uspto-grants-1978_05
Patent number
US04087422

Reaction notes

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