Hydrochloric Acid → HCID 10194185, compound

HRID 597068Notes

Reaction equation

HRID 597068 reaction equation
[CH3:1][C:2]([CH2:4][CH2:5][C:6]([OH:8])=[O:7])=O.[CH3:9][S:10][C:11]1[N:20]=[C:19]([N:21]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)N=CC)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1.Cl.O>CCOCC>[CH3:32][O:31][C:28]1[CH:27]=[C:26]2[C:25](=[CH:30][CH:29]=1)[N:21]([C:19]1[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[C:11]([S:10][CH3:9])[N:20]=1)[C:2]([CH3:1])=[C:4]2[CH2:5][C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11579Levulinic AcidHCID 86734561HCID 86734561, compound

Product 1

HCID 10194185HCID 10194185, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of laevulinic acid (7 g.), acetaldehyde N1 -(2-methylthioquinazolin-4-yl)-p-methoxyphenylhydrazone (3.5 g.) and a saturated solution of hydrogen chloride in ether (2 ml.) was heated at 95° - 100° C. for 22 hours. The mixture was poured into water (300 ml.), and the precipitated brown solid was collected by filtration and dissolved in chloroform (100 ml.). The solution was filtered and the filtrate was extracted with 2 N- ammonia solution (4 × 50 ml.). The extracts were combined and acidified to pH3 with glacial acetic acid. The mixture was filtered, and the solid crystallised from methanol to give 5-methoxy-2-methyl-1-(2-methylthioquinazolin-4-yl)indol-3-ylacetic acid, as a pale yellow crystalline solid, m.p. 175°-178° C.

Workup

  1. filtrationthe precipitated brown solid was collected by filtration
  2. dissolutiondissolved in chloroform (100 ml.)
  3. filtrationThe solution was filtered
  4. extractionthe filtrate was extracted with 2 N- ammonia solution (4 × 50 ml.)
  5. filtrationThe mixture was filtered
  6. customthe solid crystallised from methanol

Sources & evidence

ORD record
ord-24064b41c3d143549e44912a45bdf4cf
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

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