Methylamine → 2-Isopropyl-4-(N-methyl)amino-methyl thiazole

HRID 1457101Notes

Reaction equation

HRID 1457101 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]=[C:6]([CH:9]([CH3:11])[CH3:10])[S:7][CH:8]=1.[CH3:12][NH2:13]>O>[CH:9]([C:6]1[S:7][CH:8]=[C:4]([CH2:3][NH:13][CH3:12])[N:5]=1)([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 187588464-(Chloromethyl)-2-(propan-2-yl)-1,3-thiazole--hydrogen chloride (1/1)

Product 1

HCID 107496872-Isopropyl-4-(N-methyl)amino-methyl thiazoleYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 40 g of 4-(chloromethyl)-2-isopropylthiazole hydrochloride in 100 ml of water was added dropwise with stirring to 400 ml of 40% aqueous methylamine. The resulting solution was stirred for 1 h, then concentrated in vacuo. The residue was taken up in chloroform, dried over Na2 SO4, and concentrated in vacuo. Purification of the residue by silica gel chromatography using 10% methanol in chloroform provided 21.35 g (55%) of the desired compound. 1H NMR (DMSO-d6) δ 1.34 (d, J=7 Hz, 6 H), 2.56 (s, 3H), 3.30 (heptet, J=7 Hz, 1H), 4.16 (s, 2H), 7.63 (s, 1H). Mass spectrum: (M+H)+ =171.

Workup

  1. concentrationconcentrated in vacuo
  2. customdried over Na2 SO4
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-bee3c78099a2468bb6b5e99f8b5c72af
Source dataset
uspto-grants-1998_12
Patent number
US05846987

Reaction notes

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