Ethanol → 5-amino-N-methyl-1,3,4-thiadiazole-2-carboxamide

HRID 1874004Notes

Reaction equation

HRID 1874004 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]([O:9]CC)=O)=[N:4][N:3]=1.C(O)C.[CH3:15][NH2:16]>CO>[NH2:1][C:2]1[S:6][C:5]([C:7]([NH:16][CH3:15])=[O:9])=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 2756556Ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate

Product 1

HCID 580915025-amino-N-methyl-1,3,4-thiadiazole-2-carboxamideYield 102.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate (106 mg, 0.612 mmol) in methanol (1.5 mL) was added 33 wt % ethanol solution of methylamine (0.5 mL, 4.00 mmol). The mixture was stirred at room temperature for 6 h, heated to 70° C. and cooled. The mixture was concentrated, mixed with water and lyophilized to give 5-amino-N-methyl-1,3,4-thiadiazole-2-carboxamide as a white solid (99 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.69 (q, J=4.8 Hz, 1H), 7.70 (s, 2H) 2.73 (d, J=4.78 Hz, 3H); MS (ES+) m/z: 159 (M+H); LC retention time: 0.44 min (analytical HPLC Method A).

Workup

  1. temperatureheated to 70° C.
  2. temperaturecooled
  3. concentrationThe mixture was concentrated
  4. additionmixed with water

Sources & evidence

ORD record
ord-4e9d1bde5ac24aefb0ef4e7098597c79
Source dataset
uspto-grants-2012_11
Patent number
US08304539B2

Reaction notes

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