Hydrazine hydrate (1:1) → HCID 57688156, compound

HRID 2425942Notes

Reaction equation

HRID 2425942 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([C:11]2[S:15][C:14]([C:16]([O:18]C)=O)=[CH:13][CH:12]=2)=[O:10])[CH:2]=1.O.[NH2:21][NH2:22]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([C:11]2[S:15][C:14]([C:16]([NH:21][NH2:22])=[O:18])=[CH:13][CH:12]=2)=[O:10])[CH:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 37172412Methyl 5-(3-picolylcarbamoyl)thiophene-2-carboxylate

Product 1

HCID 57688156HCID 57688156, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 5-(3-picolylcarbamoyl)thiophene-2-carboxylate (860 mg, 3.11 mmol) in ethanol (34 mL) was stirred with hydrazine monohydrate (1.57 m, 31.1 mmol) at 85° C. for 12 hours. The reaction solution was concentrated and stirred with diethyl ether at 0° C. for 1 hour. The precipitated solid was recovered by filtration and washed with a liquid mixture of diethyl ether and ethanol and dried to give the desired product, 5-hydrazinocarbonylthiophene-2-carboxylic acid 3-picolylamide (yield 92%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. filtrationThe precipitated solid was recovered by filtration
  3. washwashed with a liquid mixture of diethyl ether and ethanol
  4. customdried

Sources & evidence

ORD record
ord-c43f29f53d45424ebe560671a2420e55
Source dataset
uspto-grants-2011_06
Patent number
US07968542B2

Reaction notes

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