Acetic Acid → HCID 15017642, compound

HRID 2247934Notes

Reaction equation

HRID 2247934 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-6748bf7bde6f4c23b6a7273d022628b7
Source dataset
uspto-grants-1991_08
Patent number
US05037834

Reaction notes

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