5-Chlorothiophene-2-carboxylic acid hydrazide → 2-[(5-Chloro-2-thienyl)carbonyl]-N-(2-methoxyethyl)hydrazinecarboxamide

HRID 709146Notes

Reaction equation

HRID 709146 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][NH2:10])=[O:8])=[CH:4][CH:3]=1.[N:11]([CH2:14][CH2:15][O:16][CH3:17])=[C:12]=[O:13]>C1COCC1>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][NH:10][C:12]([NH:11][CH2:14][CH2:15][O:16][CH3:17])=[O:13])=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27579235-Chlorothiophene-2-carboxylic acid hydrazideHCID 144050071-Isocyanato-2-methoxyethane

Product 1

HCID 595369432-[(5-Chloro-2-thienyl)carbonyl]-N-(2-methoxyethyl)hydrazinecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

At 50° C., 3.1 g (17.55 mmol) of 5-chlorothiophene-2-carbohydrazide were substantially suspended in 30 ml of dry THF. 1.81 g (17.90 mmol) of 1-isocyanato-2-methoxyethane dissolved in 30 ml of THF were then added dropwise. The mixture was stirred at 50° C. for 2.5 h. After cooling to RT, the solvent was removed on a rotary evaporator and the residue was triturated with diethyl ether. The crystals were filtered off with suction, washed with diethyl ether and dried under high vacuum. This gave 4.87 g (100% of theory) of the title compound.

Workup

  1. customAt 50° C.
  2. additionwere then added dropwise
  3. temperatureAfter cooling to RT
  4. customthe solvent was removed on a rotary evaporator
  5. customthe residue was triturated with diethyl ether
  6. filtrationThe crystals were filtered off with suction
  7. washwashed with diethyl ether
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-d7260b50c1ba4c6f8adb6a966d253d42
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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