4-(Chloromethyl)-N,N-dimethyl-1,3-thiazol-2-amine → (2-(Dimethylamino)thiazol-4-yl)methanol

HRID 433755Notes

Reaction equation

HRID 433755 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([N:8]([CH3:10])[CH3:9])[S:6][CH:7]=1.C1C[O:14]CC1.O>F[B-](F)(F)F.[Ag+]>[CH3:9][N:8]([C:5]1[S:6][CH:7]=[C:3]([CH2:2][OH:14])[N:4]=1)[CH3:10]

Participants

4

Reactant 2

HCID 152908844-(Chloromethyl)-N,N-dimethyl-1,3-thiazol-2-amineHCID 21881883Oxolane--water (1/1)2×

Product 1

HCID 18758920(2-(Dimethylamino)thiazol-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 159722Silver tetrafluoroborateCatalyst

Procedure

A solution of 5.186 g (29 mmol) of 4-(chloromethyl)-2-(dimethylamino)thiazole in 100 ml of 1:1 THF/H2O was cooled to 0° C. and treated dropwise with a solution of 5.73 g (29 mmol) of silver tetrafluoroborate in 50 ml of 1:1 THF/H2O. After being stirred for 1 h, the mixture was filtered, the solid mass was washed with ethyl acetate, and the combined filtrates were concentrated in vacuo. The black residue was purified by silica gel chromatography to provide 0.80 g (17%) of the desired compound (Rf 0.24, 6% methanol in chloroform) as an oil. 1H NMR (CDCl3) δ 2.67 (br, 1H), 3.09 (s, 6H), 4.54 (s, 2H), 6.35 (s, 1H). Mass spectrum: (M+H)+=159.

Workup

  1. filtrationthe mixture was filtered
  2. washthe solid mass was washed with ethyl acetate
  3. concentrationthe combined filtrates were concentrated in vacuo
  4. customThe black residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7b01613ddbe74fe488b836d0426f2a52
Source dataset
uspto-grants-2003_12
Patent number
US06667404B2

Reaction notes

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