Ethanol → HCID 12445507, compound

HRID 614345Notes

Reaction equation

HRID 614345 reaction equation
Cl.[NH2:2][C:3]1[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]3[O:16][CH2:17][O:18][C:12]=3[CH:11]=2)=[N:5][CH:6]=[CH:7][CH:8]=1.O(CC)[C:20]([S-])=[S:21].[K+].C(=O)(O)[O-].[Na+].C(O)C>O>[CH2:17]1[O:16][C:13]2[CH:14]=[CH:15][C:10]([N:9]3[C:4]4=[N:5][CH:6]=[CH:7][CH:8]=[C:3]4[NH:2][C:20]3=[S:21])=[CH:11][C:12]=2[O:18]1

Participants

6

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 2735045Potassium ethylxanthateHCID 21329318HCID 21329318, compound

Product 1

HCID 12445507HCID 12445507, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.6 g. (0.01 mole) of 3-amino-2-(3,4-methylenedioxyanilino)pyridine hydrochloride (Example 1, Step B), 1.8 g. (0.011 mole) of potassium ethyl xanthate, and 840 mg. (0.01 mole) of sodium bicarbonate in 45 ml. of ethanol and 10 ml. of water was heated at reflux for 3.5 hours. There was added 3 ml. of 2.5 N sodium hydroxide solution and the mixture was filtered. The filtrate was acidified with acetic acid and the precipitated product was collected (500 mg., m.p. 278° C.). After recrystallization from dioxane there was obtained 1,3-dihydro-3-(3,4-methylenedioxyphenyl)imidazo[4,5-b]pyridin-2-thione, m.p. 285° C.

Workup

  1. additionA mixture of 2.6 g
  2. temperatureat reflux for 3.5 hours
  3. additionThere was added 3 ml
  4. filtrationof 2.5 N sodium hydroxide solution and the mixture was filtered
  5. customthe precipitated product was collected (500 mg., m.p. 278° C.)
  6. customAfter recrystallization from dioxane

Sources & evidence

ORD record
ord-cbcf166adf574841b547098570e23f24
Source dataset
uspto-grants-1979_03
Patent number
US04144341

Reaction notes

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