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

HRID 220682Notes

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

Conditions

Temperature: 50 °C

Procedure

A quantity of 3.1 g (17.55 mmol) of 5-chlorothiophene-2-carbohydrazide was suspended largely finely in 30 ml of dry THF at 50° C. Then 1.81 g (17.90 mmol) of 1-isocyanato-2-methoxyethane in solution in 30 ml of THF were 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 admixed with diethyl ether. The crystals were filtered off with suction, washed with diethyl ether and dried in an HV. This gave 4.87 g (100% of theory) of the title compound.

Workup

temperatureAfter cooling to RT
customthe solvent was removed on a rotary evaporator
filtrationThe crystals were filtered off with suction
washwashed with diethyl ether
customdried in an HV

Sources & evidence

ORD record: ord-a3e48efb531e47629366d416dc539f23
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202895B2

Reaction notes

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