Methylhydrazine → HCID 12492956, compound

HRID 1695460Notes

Reaction equation

HRID 1695460 reaction equation
[CH3:1][O:2][C:3]([C:5]#[C:6][C:7]([O:9][CH3:10])=[O:8])=[O:4].[CH3:11][NH:12][NH2:13]>C(OCC)C>[CH3:1][O:2][C:3](=[O:4])/[C:5](/[N:12]([CH3:11])[NH2:13])=[CH:6]\[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 12492956HCID 12492956, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a solution of dimethylacetylene dicarboxylate (50.0 g, 344.8 mmol) in diethylether (1 L) under argon at 0° C. was added a solution of methylhydrazine (18.52 mL, 344.8 mL) in diethylether (100 mL) and the resulting mixture stirred for 2 h. The precipitate was filtered off, dissolved in ethanol (300 mL) at 50° C. and then the solution cooled to −20° C. whereupon the solid was filtered off and dried to afford the title compound (46.8 g, 72%) as a light yellow solid. MS: m/e=189.3 [M+H]+.

Workup

  1. filtrationThe precipitate was filtered off
  2. dissolutiondissolved in ethanol (300 mL) at 50° C.
  3. filtrationwas filtered off
  4. customdried

Sources & evidence

ORD record
ord-b9474d8ed8ff4e51b21820ec25bdb144
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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