Hydrazine hydrate (1:1) → 5-(hydrazinecarbonyl)-N-[4-(2-hydroxyethylcarbamoyl)benzyl]thiophene-2-carboxamide

HRID 337382Notes

Reaction equation

HRID 337382 reaction equation
OCCNC([N:7]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:8]([C:10]1[S:14][C:13]([C:15]([O:17]C)=O)=[CH:12][CH:11]=1)=[O:9])=O.[OH2:26].[NH2:27][NH2:28]>C(O)C>[NH:27]([C:15]([C:13]1[S:14][C:10]([C:8]([NH:7][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:8](=[O:9])[NH:7][CH2:19][CH2:20][OH:26])=[CH:24][CH:25]=2)=[O:9])=[CH:11][CH:12]=1)=[O:17])[NH2:28]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 117698961Methyl 5-[-(2-hydroxyethylcarbamoyl)benzylcarbamoyl]thiophene-2-carboxylate

Product 1

HCID 676353705-(hydrazinecarbonyl)-N-[4-(2-hydroxyethylcarbamoyl)benzyl]thiophene-2-carboxamideYield 185.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.73 g (2.02 mmol) of methyl 5-[-(2-hydroxyethylcarbamoyl)benzylcarbamoyl]thiophene-2-carboxylate in 12 mL of ethanol was mixed with 1.67 mL (34.43 mmol) of hydrazine monohydrate and heated under reflux for 9 hours. The reaction solution was cooled with ice, and the precipitated solid was collected by filtration, washed with ethanol and dried under reduced pressure to obtain the desired product (0.68 g, yield 93%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 9 hours
  3. temperatureThe reaction solution was cooled with ice
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with ethanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-4c763acdbabe43a4ac8dd3a05e9d3ff3
Source dataset
uspto-grants-2014_11
Patent number
US08889732B2

Reaction notes

Loading…