Acetic Acid → 3-(Dimethylaminomethyl)-2-(methoxycarbonylamino)-6-(phenylthio) imidazo [1,2-a] pyridine

HRID 1413431Notes

Reaction equation

HRID 1413431 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][N:9]2[CH:21]=1)=[O:4].[CH3:22][NH:23][CH3:24].C=O.[C:27](O)(=O)C>C(=O)(O)[O-].[Na+]>[CH3:22][N:23]([CH2:27][C:21]1[N:9]2[CH:10]=[C:11]([S:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=[CH:13][C:8]2=[N:7][C:6]=1[NH:5][C:3]([O:2][CH3:1])=[O:4])[CH3:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 12414300Methyl [6-(phenylsulfanyl)imidazo[1,2-a]pyridin-2-yl]carbamate

Product 1

HCID 545555143-(Dimethylaminomethyl)-2-(methoxycarbonylamino)-6-(phenylthio) imidazo [1,2-a] pyridine

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

2-(Methoxycarbonylamino)-6-(phenylthio) imidazo [1,2-a] pyridine (0.75 gm.) is added to a solution of 50% aqueous dimethylamine (0.215 gm., 37% formaldehyde (0.19 gm.) and acetic acid (0.35 g.) and heated at 50° C. for 3 hours. After cooling, the reaction mixture is diluted with aqueous sodium bicarbonate and the resultant precipitate is collected by filtration. After drying, the crude product is recrystallized from ethyl acetate to yield 3-(dimethylaminomethyl)-2-(methoxycarbonylamino)-6-(phenylthio) imidazo [1,2-a] pyridine m.p. 172°-175° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resultant precipitate is collected by filtration
  3. customAfter drying
  4. customthe crude product is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-05dabc1b73884d4f8fca533e33e4d804
Source dataset
uspto-grants-1981_02
Patent number
US04250174

Reaction notes

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