Hydrochloric Acid → HCID 20145058, compound

HRID 648607Notes

Reaction equation

HRID 648607 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[C:5]([C:7]([O:9]CC)=O)[N:6]=1.[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][NH2:22].Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)CO.O>[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[C:5]([C:7](=[O:9])[NH:22][CH2:21][CH2:20][N:19]([CH3:23])[CH3:18])[N:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 66053N,N-DimethylethylenediamineHCID 20144988HCID 20144988, compound

Product 1

HCID 20145058HCID 20145058, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 2-amino-5-(2-pyridyl)-4-thiazolecarboxylate (2.49 g) in ethyleneglycol (10 ml) were added N,N-dimethylethylenediamine (1.76 g) and 36% hydrochloric acid (0.5 ml) and the mixture was stirred at 80° C. for 2 hours. The reaction mixture was poured into water (50 ml), adjusted to pH 8 with aqueous potassium carbonate and extracted with chloroform. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from acetonitrile to give 2-amino-4-[N-[2-(N,N-dimethylamino)ethyl]carbamoyl]-5-(2-pyridyl)thiazole (2.0 g).

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-2160203f45524809ade017706ea50f28
Source dataset
uspto-grants-1988_04
Patent number
US04735957

Reaction notes

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