Water → HCID 69413636, compound

HRID 1417155Notes

Reaction equation

HRID 1417155 reaction equation
[C:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)(=O)[CH3:2].[C:9]([CH2:11][C:12]([O:14][CH3:15])=[O:13])#[N:10].C([O-])(=O)C.[NH4+].O>C(O)(=O)C.C1(C)C=CC=CC=1>[C:9](/[C:11](=[C:1](/[C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)\[CH3:2])/[C:12]([O:14][CH3:15])=[O:13])#[N:10]

Participants

7

Reactant 4

HCID 962WaterHCID 69202-AcetylthiopheneHCID 7747Methyl cyanoacetateHCID 517165Ammonium Acetate

Product 1

HCID 69413636HCID 69413636, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

400 g of 2-acetylthiophene, 314 g of methyl cyanoacetate and 48.8 g of ammonium acetate were dissolved in a mixture of 153 ml of acetic acid and 1.5 l of toluene, and the resulting reaction solution was refluxed under heating for 8 hours while water was removed. The reaction solution was washed sufficiently with water and then dried over anhydrous magnesium sulfate. Removal of the solvent by distillation was followed by vacuum distillation (b.p. 110°-140° C./0.05 mmHg) to give 263.4 g of methyl 2-cyano-3-(2-thienyl)crotonate. (Yield 40%)

Workup

  1. customthe resulting reaction solution
  2. temperaturewas refluxed
  3. customwas removed
  4. washThe reaction solution was washed sufficiently with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customRemoval of the solvent
  7. distillationby distillation
  8. distillationwas followed by vacuum distillation (b.p. 110°-140° C./0.05 mmHg)

Sources & evidence

ORD record
ord-9b0c0cbe08904417ad86af77eee770c3
Source dataset
uspto-grants-1999_03
Patent number
US05877120

Reaction notes

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