Thiophene-2-carbohydrazide → 4-cyclopropyl-5-thien-2-yl-4H-1,2,4-triazole-3-thiol

HRID 273120

Reaction equation

HRID 273120 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][NH2:9])=O.[N:10]([CH:13]1[CH2:15][CH2:14]1)=[C:11]=[S:12]>CC(O)C>[CH:13]1([N:10]2[C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[N:8][NH:9][C:11]2=[S:12])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 73098Thiophene-2-carbohydrazideHCID 92463Cyclopropyl isothiocyanate

Product 1

HCID 49624414-cyclopropyl-5-thien-2-yl-4H-1,2,4-triazole-3-thiol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

To a slurry of thiophene-2-carboxylic acid hydrazide (866 mg, 6.09 mmol) in iPrOH (25 ml) was added isothiocyanato-cyclopropane (602 mg, 6.08 mmol). The mixture was stirred at 70° C. for 72 h and then cooled to room temperature. The white precipitate was filtered off and suspended in a MeOH:H2O (9:1, 40 ml) together with aq. NaOH (2%, 5 ml). The reaction mixture was stirred at 70° C. overnight and then cooled to room temperature. The pH was adjusted to around 4 with aq. HCl (1N). The formed white precipitate was filtered off, washed with water and dried under vacuum (829 mg, 61%). 1H NMR (CD3OD), δ (ppm): 7.67 (dd, 1H), 7.63 (dd, 1H), 7.17 (dd, 1H), 3.15 (m, 1H), 1.14 (m, 2H), 0.86 (m, 2H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe white precipitate was filtered off
  3. stirringThe reaction mixture was stirred at 70° C. overnight
  4. temperaturecooled to room temperature
  5. filtrationThe formed white precipitate was filtered off
  6. washwashed with water
  7. customdried under vacuum (829 mg, 61%)

Sources & evidence

ORD record
ord-500a75d4ebd548c2b2f7c030828cdc1a
Source dataset
uspto-grants-2008_11
Patent number
US07456200B2

Linked notes

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