Triethylamine → N-benzyl-2-(N'-hydroxycarbamimidoyl)-4-methylthiazole-5-carboxamide

HRID 2381798Notes

Reaction equation

HRID 2381798 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]#[N:17])=[N:13][C:12]=1[CH3:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21].C(N(CC)CC)C>C(O)C>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16](=[N:20][OH:21])[NH2:17])=[N:13][C:12]=1[CH3:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 68492000N-benzyl-2-cyano-4-methylthiazole-5-carboxamide

Product 1

HCID 136404881N-benzyl-2-(N'-hydroxycarbamimidoyl)-4-methylthiazole-5-carboxamideYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-benzyl-2-cyano-4-methylthiazole-5-carboxamide (0.15 g, 0.58 mmol) and hydroxylamine hydrochloride (0.09 g, 1.28 mmol) in ethanol (7 mL) was added triethylamine (0.2 mL, 1.43 mmol). The reaction mixture was heated to reflux for 3 hour, cooled to ambient temperature and concentrated in vacuo. The solid was washed with water and dried to afford the title compound in 70% yield (0.12 g): 1H NMR (300 MHz, CDCl3) δ 7.43-7.18 (m, 5H), 6.42 (br s, 1H), 5.74 (br s, 2H), 4.54 (d, J=5.3 Hz, 2H), 2.63 (s, 3H); MS (ES+) m/z 291.1 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hour
  3. concentrationconcentrated in vacuo
  4. washThe solid was washed with water
  5. customdried

Sources & evidence

ORD record
ord-fb68ef30740b4b08aa7fad777cde5f4f
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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