Furan, 2-(bromomethyl)tetrahydro- → 4,5-Dimethyl-3-(tetrahydrofuran-2-ylmethyl)-1,3-thiazol-2(3H)-ylideneamine hydrobromide

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([CH3:8])=[C:5]([CH3:7])[N:6]=1.[Br:9][CH2:10][CH:11]1[CH2:15][CH2:14][CH2:13][O:12]1>>[BrH:9].[CH3:7][C:5]1[N:6]([CH2:10][CH:11]2[CH2:15][CH2:14][CH2:13][O:12]2)[C:2](=[NH:1])[S:3][C:4]=1[CH3:8]

Participants

Reactant 2

HCID 14501Furan, 2-(bromomethyl)tetrahydro-

HCID 732382-Amino-4,5-dimethyl-1,3-thiazole

Product 1

HCID 686217604,5-Dimethyl-3-(tetrahydrofuran-2-ylmethyl)-1,3-thiazol-2(3H)-ylideneamine hydrobromide

Procedure

A mixture of 2-amino-4,5-dimethylthiazole and 2-(bromomethyl)tetrahydrofuran were processed using the method described in Example 12A to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.43-1.64 (m, 1H) 1.73-2.00 (m, 3H) 2.17 (s, 3H) 2.19 (s, 3H) 3.53-3.68 (m, 1H) 3.71-3.85 (m, 1H) 3.91-4.17 (m, 3H) 9.34 (s, 1H),), MS (DCI/NH3) m/z 212 (M+H)+.

Sources & evidence

ORD record: ord-fe8c0ca38329459780cca436ad88484e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841334B2

Reaction notes

Loading…