1,4-Dioxane hydrochloride → 4-((2-Methoxyethoxy)methyl)thiazol-2-amine hydrochloride

HRID 1020241Notes

Reaction equation

HRID 1020241 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[N:12]=1)(C)(C)C.[ClH:20].O1CCOCC1>>[ClH:20].[CH3:18][O:17][CH2:16][CH2:15][O:14][CH2:13][C:11]1[N:12]=[C:8]([NH2:7])[S:9][CH:10]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86622744tert-Butyl-4-((2-methoxyethoxy)methyl)thiazol-2-ylcarbamate

Product 1

HCID 866227454-((2-Methoxyethoxy)methyl)thiazol-2-amine hydrochloride

Procedure

Carbamate III (Example 4) (225 mg, 781 μmol) was stirred at ambient temperature with HCl/dioxane (4 M, 4 ml) for 18 hours. Volatiles were removed under reduced pressure and the residue was azeotroped several times with toluene. 1H NMR (300 MHz, CD3OD) δ 3.37 (s, 1H), 3.55-3.59 (m, 2H), 3.64-3.68 (m, 2H), 4.43 (s, 2H), 6.82 (s, 1H).

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe residue was azeotroped several times with toluene

Sources & evidence

ORD record
ord-53caa880c8414723928d96d242dc380f
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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