2-(Ethoxymethylene)propanedinitrile → N-(1,3-Benzothiazol-5-yl)acetamide

HRID 1242042Notes

Reaction equation

HRID 1242042 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[SH:12])[NH:5][C:6](=[O:8])[CH3:7].[CH2:13](OC=C(C#N)C#N)C>CC(O)=O>[C:6]([NH:5][C:4]1[CH:9]=[CH:10][C:11]2[S:12][CH:13]=[N:1][C:2]=2[CH:3]=1)(=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 21937579N-(3-Amino-4-sulfanylphenyl)acetamide

Product 1

HCID 285205N-(1,3-Benzothiazol-5-yl)acetamideYield 17%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of intermediate 3′-amino-4′-mercaptoacetanilide in HOAc (50 mL) was added ethoxymethylene malononitrile (1.95 g, 16 mmol) and the resulting mixture was refluxed at 125° C. for 5 h. After cooling, the product mixture was concentrated under reduced pressure, and the residue was partitioned between saturated aqueous NaHCO3 and EtOAc. The aqueous phase was extracted with EtOAc, and the combined extracts were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by chromatography on silica gel, eluting with EtOAc-Hex (0:100 to 50:50) to give the title compound (508 mg, 17%) as a yellow solid. 1H-NMR (DMSO-d6): δ 9.35 (1H, s), 8.53 (1H, s), 8.10 (1H, d), 7.63 (1H, d), 2.15 (3H, s).

Workup

  1. temperatureAfter cooling
  2. concentrationthe product mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between saturated aqueous NaHCO3 and EtOAc
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washthe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel
  9. washeluting with EtOAc-Hex (0:100 to 50:50)

Sources & evidence

ORD record
ord-0e77c3d872a748bd842f90cd03aab956
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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