Acetic Acid → HCID 15017641, compound

HRID 2247933Notes

Reaction equation

HRID 2247933 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]2[S:9][CH:10]=[C:11]([CH2:13][CH2:14][NH2:15])[N:12]=2)[CH:2]=1.[C:16](O)(=O)C.C=O>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]2[S:9][C:10]3[CH2:16][NH:15][CH2:14][CH2:13][C:11]=3[N:12]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 712Formaldehyde2×HCID 15017652N-[4-(2-Aminoethyl)-2-thiazolyl]-3-pyridinamine

Product 1

HCID 15017641HCID 15017641, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(3-Pyridyl)amino-4-(2-aminoethyl)thiazole (0.50 g, from preceding preparation) and acetic acid (0.19 ml, 3.3 mmol) were dissolved in methanol (23 ml) and treated with formaldehyde (0.19 ml of a 37% aqueous solution, 2.3 mmol). The reaction was allowed to stir at room temperatue for 18 hours, at which point additional formaldehyde (0.02 ml of a 37% aqueous solution, 0.25 mmol) was added. After an additional 2 hours, the reaction mixture was filtered; the filtrate was concentrated in vacuo, dissolved in aqueous base, and extracted with methylene chloride. The organic extracts were dried over sodium sulfate and concentrated to provide the title product (310 mg, 1.3 mmol, 57% yield).

Workup

  1. additionwas added
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutiondissolved in aqueous base
  5. extractionextracted with methylene chloride
  6. dry with materialThe organic extracts were dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4646b92d09f144c6acbc2447f155aaa0
Source dataset
uspto-grants-1991_08
Patent number
US05037834

Reaction notes

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