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

HRID 443152Notes

Reaction equation

HRID 443152 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-0eb609f5b5034365803e6feb43b75c96
Source dataset
uspto-grants-1999_04
Patent number
US05892052

Reaction notes

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