2-Bromoethyl methyl ether → HCID 66858523, compound

HRID 78447Notes

Reaction equation

HRID 78447 reaction equation
[C:1]([C:5]1[S:9][C:8]([NH2:10])=[N:7][C:6]=1[CH3:11])([CH3:4])([CH3:3])[CH3:2].[CH3:12][O:13][CH2:14][CH2:15]Br>C(Cl)Cl.CO>[C:1]([C:5]1[S:9][C:8](=[NH:10])[N:7]([CH2:15][CH2:14][O:13][CH3:12])[C:6]=1[CH3:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 10815365-tert-Butyl-4-methyl-thiazol-2-ylamine

Product 1

HCID 66858523HCID 66858523, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5-tert-butyl-4-methylthiazole-2-ylamine (1.5 g, 8.8 mmol) and 2-bromoethyl methyl ether (0.91 mL, 9.7 mmol) was warmed to 85° C. and allowed to stir for 24 hours. The crude material was dissolved in ˜5 mL of a 1:1 mixture of CH2Cl2 and CH3OH and a small amount of silica gel was added. This mixture was concentrated to dryness and the residue was purified via flash column chromatography (SiO2, 9:1:0.1 CH2Cl2:CH3OH:NH4OH) to afford the title compound (1.0 g, 4.4 mmol, 50% yield). 1H NMR (300 MHz, CD3OD) δ ppm 1.41 (s, 9H) 2.38 (s, 3H) 3.35 (s, 3H) 3.66 (t, J=4.70 Hz, 2H) 4.16 (t, J=4.70 Hz, 2H); MS (DCI/NH3) m/z 229 (M+H)+.

Workup

  1. additiona small amount of silica gel was added
  2. concentrationThis mixture was concentrated to dryness
  3. customthe residue was purified via flash column chromatography (SiO2, 9:1:0.1 CH2Cl2:CH3OH:NH4OH)

Sources & evidence

ORD record
ord-ea50addb0e204b0289ffd612d59bd8dd
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

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