Toluene → HCID 14666710, compound

HRID 648556Notes

Reaction equation

HRID 648556 reaction equation
[OH-:1].O[C:3]1[C:11]2[CH:10]=[CH:9][N+:8]3[CH:12]=[CH:13]S[C:7]=3[C:6]=2[S:5][C:4]=1C1C=CC=CC=1.[CH3:21][O:22][CH2:23][CH2:24][NH:25][C:26](=[O:29])[C:27]#[CH:28].[C:30]1(C)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH3:21][O:22][CH2:23][CH2:24][NH:25][C:26]([C:27]1[CH:28]=[C:13]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:12](=[O:1])[N:8]2[C:7]=1[C:6]1[S:5][CH:4]=[CH:3][C:11]=1[CH:10]=[CH:9]2)=[O:29]

Participants

4

Reactant 3

HCID 1140TolueneHCID 19020425HCID 19020425, compoundHCID 19020473N-(2-Methoxyethyl)prop-2-ynamide

Product 1

HCID 14666710HCID 14666710, compound

Procedure

70.8 mg of 7-hydroxy-8-phenylthiazolo[3,2-a]thieno[2,3-c]pyridinium hydroxide (internal salt) and 38.2 ml of N-(2-methoxyethyl)-2-propynamide were heated for a long time in toluene under argon. The solvent was removed in vacuo and the residue was chromatographed on silica gel. After recrystallization from ethyl acetate, there was obtained N-(2-methoxyethyl)-7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxamide as yellow crystals of m.p. 201°-202°.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed on silica gel
  3. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-949422c904704624bdd30ca9f2fe26c2
Source dataset
uspto-grants-1988_04
Patent number
US04735940

Reaction notes

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