Acetic Acid → HCID 15017642, compound

HRID 249302Notes

Reaction equation

HRID 249302 reaction equation
[C:1]1([NH:7][C:8]2[S:9][CH:10]=[C:11]([CH2:13][CH2:14][NH2:15])[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](O)(=O)C.C=O>CO>[C:1]1([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]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 11797847HCID 11797847, compound

Product 1

HCID 15017642HCID 15017642, compoundYield 382.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-phenylamino-4-(2-aminoethyl)thiazole (0.30 g, 1.37 mmol) in methanol (15 ml) was treated with acetic acid (0.02 ml, 0.35 mmol) and formaldehyde (0.11 ml of a 37% aqueous solution, 1.37 mmol). After 20 minutes, the reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated in vacuo to provide a glassy solid (0.31 g, 1.34 mmol, 98% yield) which was used without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6cb15f2c0b164a2dbaa5600073c3b1dc
Source dataset
uspto-grants-1993_05
Patent number
US05214051

Reaction notes

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