2-Methoxyethylamine → HCID 178495976, compound

HRID 1734031Notes

Reaction equation

HRID 1734031 reaction equation
I.[C:2]([NH:5][CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[N:14]=[C:15]([NH:18][C:19](=[NH:22])SC)[S:16][CH:17]=2)[CH:10]=[CH:11][CH:12]=1)(=[O:4])[CH3:3].[CH3:23][O:24][CH2:25][CH2:26][NH2:27]>C(O)C>[C:2]([NH:5][CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[N:14]=[C:15]([N:18]=[C:19]([NH2:22])[NH:27][CH2:26][CH2:25][O:24][CH3:23])[S:16][CH:17]=2)[CH:10]=[CH:11][CH:12]=1)(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 178504024HCID 178504024, compound

Product 1

HCID 178495976HCID 178495976, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(3-acetylaminomethylphenyl)-2-(2-methyl-1-isothioureido)thiazole hydriodide (2.0 g) and 2-methoxyethylamine (5 ml) in ethanol (50 ml) was refluxed for 25 hours. The solvent was removed under reduced pressure and the residue was suspended in water (100 ml). The mixture was alkalized with 30% aqueous potassium carbonate solution and then extracted with a mixture of ethyl acetate (200 ml) and tetrahydrofuran (50 ml). The extract was dried with magnesium sulfate. The solvent was removed under reduced pressure and the residue was crystallized from ethyl acetate. Recrystallization from ethyl acetate afforded 4-(3-acetylaminomethylphenyl)-2-[[(amino)(2-methoxyethylamino)methylene]amino]thiazole (0.65 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with a mixture of ethyl acetate (200 ml) and tetrahydrofuran (50 ml)
  3. dry with materialThe extract was dried with magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was crystallized from ethyl acetate
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-5e70207d28654ae497969a5266be7b96
Source dataset
uspto-grants-1996_07
Patent number
US05532258

Reaction notes

Loading…