Acetic Acid → HCID 15017641, compound

HRID 249301Notes

Reaction equation

HRID 249301 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 temperature 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-085488d602404228a106cab0f6201258
Source dataset
uspto-grants-1993_05
Patent number
US05214051

Reaction notes

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