Ethylamine → 5-Amino-N-ethyl-1,3,4-thiadiazole-2-carboxamide

HRID 1874005Notes

Reaction equation

HRID 1874005 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]([O:9]CC)=O)=[N:4][N:3]=1.[CH2:12]([NH2:14])[CH3:13]>CO>[NH2:1][C:2]1[S:6][C:5]([C:7]([NH:14][CH2:12][CH3:13])=[O:9])=[N:4][N:3]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 2756556Ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate

Product 1

HCID 580916185-Amino-N-ethyl-1,3,4-thiadiazole-2-carboxamideYield 100.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate (200 mg, 1.155 mmol) in methanol (1.5 mL) was added a 70% aqueous solution of ethylamine (0.5 mL, 6.29 mmol). The mixture was stirred at room temperature overnight, concentrated, mixed with water and lyophilized to give 5-amino-N-ethyl-1,3,4-thiadiazole-2-carboxamide as a yellowish solid (200 mg). MS (ES+) m/z: 173 (M+H); LC retention time: 0.70 min (analytical HPLC Method A).

Workup

  1. concentrationconcentrated
  2. additionmixed with water

Sources & evidence

ORD record
ord-093dfde1f6e2403abf007fe1253da48b
Source dataset
uspto-grants-2012_11
Patent number
US08304539B2

Reaction notes

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