Dimethyl acetylenedicarboxylate → HCID 2741096, compound

HRID 728338Notes

Reaction equation

HRID 728338 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][NH2:14].[CH3:15][O:16][C:17]([C:19]#[C:20][C:21](OC)=[O:22])=[O:18].C[O-].[Na+].[Na]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:21](=[O:22])[CH:20]=[C:19]([C:17]([O:16][CH3:15])=[O:18])[NH:14]1

Participants

6

Reactant 4

HCID 12980Dimethyl acetylenedicarboxylateHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 2741096HCID 2741096, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 30.1 g (0.123 mole) of 2,6-dichloro-4-trifluoromethylphenylhydrazine in 75 ml of methanol was added dropwise with stirring a solution of 18.5 g (0.13 mole) of dimethylacetylene dicarboxylate dissolved in 75 ml of methanol. The reaction mixture was stirred for 2.5 hrs. at 10°-20° C. The brown mixture was then added slowly, over a period of 50 min., to a stirred solution of sodium methoxide (made by dissolving 11.0 g (0.478 mole) of sodium in 400 ml of anhydrous methanol). After stirring for an additional period of 1.5 hr, the solution was concentrated under a partial vacuum and acidified with 100 ml of 4N hydrochloric acid. The precipitated solid was filtered, washed with water and air dried to afford 28.4 g (65 percent yield) of a tan colored solid, mp 245°-246° C., which was recrystallized from methanol to give a solid, mp 249°-250° C.

Workup

  1. customat 10°-20° C
  2. stirringAfter stirring for an additional period of 1.5 hr
  3. concentrationthe solution was concentrated under a partial vacuum
  4. filtrationThe precipitated solid was filtered
  5. washwashed with water and air
  6. customdried

Sources & evidence

ORD record
ord-4970eecf52734ca398e5ec58defb8858
Source dataset
uspto-grants-1991_09
Patent number
US05047550

Reaction notes

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