Triethylamine → Ethyl 2-(1-methyl-2-(thiophen-2-ylmethylcarbamoyl)hydrazinyl)acetate

HRID 1254480Notes

Reaction equation

HRID 1254480 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8](=[O:19])OC1C=CC([N+]([O-])=O)=CC=1.[CH3:20][N:21]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[NH2:22].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[CH3:20][N:21]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[NH:22][C:8](=[O:19])[NH:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 20288078Ethyl 2-(1-methylhydrazinyl)acetateHCID 670755344-Nitrophenyl thiophen-2-ylmethylcarbamate

Product 1

HCID 67088516Ethyl 2-(1-methyl-2-(thiophen-2-ylmethylcarbamoyl)hydrazinyl)acetateYield 46.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 4-nitrophenyl thiophen-2-ylmethylcarbamate (Compound XII-1) 3.14 g (11 mmol) in dichloromethane 20 ml, ethyl 2-(1-methylhydrazinyl)acetate (Compound XV-2) 2.98 g (22.6 mmol) and triethylamine 2.36 ml (17 mmol) was added at 0° C. and stirred at additional 4.5 hours. The reaction mixture was diluted with ethyl acetate 100 ml and washed with water 10 ml and brine 75 ml. The organic phase was dried with magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was submitted to silcagel chromatography to obtain the title compound 1.38 g (45%).

Workup

  1. washwashed with water 10 ml and brine 75 ml
  2. dry with materialThe organic phase was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9f5ca75a34e44eedab4fb836d3ec2571
Source dataset
uspto-grants-2013_06
Patent number
US08455488B2

Reaction notes

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