4-(Methylthio)-o-anisic acid → HCID 178418519, compound

HRID 3848Notes

Reaction equation

HRID 3848 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([S:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5](O)=O.[NH2:14][C:15]1[C:16](=[O:22])[NH:17][N:18]=[CH:19][C:20]=1[NH2:21]>>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([S:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]1[N:14]=[C:15]2[C:16](=[O:22])[NH:17][NH:18][CH:19]=[C:20]2[N:21]=1

Participants

3

Reactant 2

HCID 6433294-(Methylthio)-o-anisic acidHCID 127052174,5-Diaminopyridazin-3(2H)-one

Product 1

HCID 178418519HCID 178418519, compound

Conditions

Temperature
50 °C

Procedure

Two grams of 2-methoxy-4-methylmercapto-benzoic acid are suspended in 20 ml of polyphosphoric acid, and 1.2 gm of 4,5-diamino-2H-pyridazin-3-one are added thereto with stirring at 50° C. The mixture is heated for 90 minutes to 100°-110° C. and then poured onto ice water, and the product which is precipitated on stirring is subjected to suction filtration. The mother liquor is extracted with ethyl acetate, after which the aqueous phase is made ammoniacal and extracted again with ethyl acetate. The last ethyl acetate phase is evaporated. The residue is combined with the above solid product and purified by chromatography on silica gel [eluant: methylene chloride/ethanol (100:0 to 100:3)].

Workup

  1. temperatureThe mixture is heated for 90 minutes to 100°-110° C.
  2. additionpoured onto ice water
  3. customthe product which is precipitated
  4. stirringon stirring
  5. filtrationis subjected to suction filtration
  6. extractionThe mother liquor is extracted with ethyl acetate
  7. extractionextracted again with ethyl acetate
  8. customThe last ethyl acetate phase is evaporated
  9. custompurified by chromatography on silica gel [eluant: methylene chloride/ethanol (100:0 to 100:3)]

Sources & evidence

ORD record
ord-e5f252377ae24090a434bf5416e54651
Source dataset
uspto-grants-1988_02
Patent number
US04722929

Reaction notes

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