Ethylamine → Methyl({2-[2-(propan-2-yl)-1,3-thiazol-4-yl]ethyl})amine

HRID 850570Notes

Reaction equation

HRID 850570 reaction equation
[CH:1]([C:4]1[S:5][CH:6]=[C:7]([CH2:9][CH2:10]O)[N:8]=1)([CH3:3])[CH3:2].CS(Cl)(=O)=O.[CH2:17]([N:19](CC)CC)C.C(N)C>O1CCCC1.C(OCC)(=O)C>[CH:1]([C:4]1[S:5][CH:6]=[C:7]([CH2:9][CH2:10][NH:19][CH3:17])[N:8]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 106310152-(2-Isopropylthiazol-4-yl)ethanol

Product 1

HCID 18758998Methyl({2-[2-(propan-2-yl)-1,3-thiazol-4-yl]ethyl})amine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.0 g (12 mmol) of 2-isopropyl-4-(hydroxyethyl)thiazole in 50 ml of tetrahydrofuran was treated with 1.34 g (12 mmol) of methanesulfonyl chloride. The resulting solution was treated dropwise with 3.4 ml (24 mmol) of triethylamine and stirred at ambient temperature for 1 h. A portion (25 ml) of the resulting solution was added to 50 ml of aqueous ethylamine (70% in H2O) with rapid stirring. After addition, the mixture was heated to reflux for 2 h, allowed to cool, diluted with ethyl acetate, washed with aqueous NaHCO3 and saturated brine, dried over Na2SO4, and concentrated in vacuo to provide the crude desired compound. Purification of the residue by silica gel chromatography using 5% methanol in chloroform, 0.52 g (48%) of the desired compound. 1H NMR (CDCl3) δ 1.38 (d, J=7 Hz, 3 H), 2.46 (s, 3 H), 2.93 (s, 4 H), 3.30 (heptet, J=7 Hz, 1 H), 6.79 (s, 1 H). Mass spectrum: (M+H)+ =185.

Workup

  1. additionAfter addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 2 h
  4. temperatureto cool
  5. washwashed with aqueous NaHCO3 and saturated brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ae8e265e4c34b86b21740290bd770af
Source dataset
uspto-grants-2000_01
Patent number
US06017928

Reaction notes

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