Ethyl Thioglycolate → 3-Amino-4-cyano-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester

HRID 1990071Notes

Reaction equation

HRID 1990071 reaction equation
[C:1]([C:3]([C:10]#[N:11])=[C:4](Cl)[C:5]([F:8])([F:7])[F:6])#[N:2].FF.[SH:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])(=O)C.[K+]>O.C(O)C>[CH2:19]([O:18][C:16]([C:15]1[S:14][C:4]([C:5]([F:8])([F:7])[F:6])=[C:3]([C:10]#[N:11])[C:1]=1[NH2:2])=[O:17])[CH3:20]

Participants

7

Reactant 4

HCID 12185Ethyl ThioglycolateHCID 24524FluorineHCID 517044Potassium AcetateHCID 12591685(1-Chloro-2,2,2-trifluoroethylidene)propanedinitrile

Product 1

HCID 685236583-Amino-4-cyano-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Combine 1,1-dicyano-2-chloro-2-(trifluoromethyl)ethylene (0.554 mmol) (prepared by the method of Middleton, J. Fluorine Chem., 20, 1982, p 397-418) and ethanol in a 50 ml flask. Add ethyl 2-mercaptoacetate (0.554 mmol) and potassium acetate (0.831 mmol) and heat to 60-70° C. for 30-40 minutes. Cool the reaction and add water. Product crystallizes as yellowish needles. Filter crystals and wash with 1:1 ethanol/water. Dry solid under reduced pressure to give the title compound as light yellow crystals: 1H NMR (400 MHz, CDCl3) δ 5.88 (s, 2H), 4.36 (q, 2H, J=7.2 Hz), 1.38 (t, 3H, J=7.0 Hz), MS found (M−1) 262.9.

Workup

  1. temperatureCool
  2. customthe reaction
  3. customProduct crystallizes as yellowish needles
  4. filtrationFilter crystals
  5. washwash with 1:1 ethanol/water
  6. customDry solid under reduced pressure

Sources & evidence

ORD record
ord-7452cf2f27f34e108f567c0913f35af0
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

Loading…