Cyanoacetic acid → 2-cyano-N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide

HRID 2094933Notes

Reaction equation

HRID 2094933 reaction equation
[C:1]1([C:7]2[S:11][C:10]([NH2:12])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]([CH2:15][C:16](O)=[O:17])#[N:14].CCN=C=NCCCN(C)C.Cl>C(#N)C.Cl>[C:13]([CH2:15][C:16]([NH:12][C:10]1[S:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][N:9]=1)=[O:17])#[N:14]

Participants

6

Reactant 3

HCID 9740Cyanoacetic acidHCID 2194082-Amino-5-phenyl-1,3,4-thiadiazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 574224092-cyano-N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

5-phenyl-1,3,4-thiadiazol-2-amine (600 mg, 3.3 mmol), cyano acetic acid (300 mg, 3.6 mmol), and EDC-HCl (861 mg, 4.5 mmol) were stirred in acetonitrile (15 mL) at room temperature for 2 hours. The mixture was diluted with aqueous 1N HCl and the aqueous phase was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with ethyl acetate/hexanes (1/9) to afford 2-cyano-N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide as a white solid which was used without further purification.

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with ethyl acetate/hexanes (1/9)

Sources & evidence

ORD record
ord-4960c4daaf4846e584ab2f0f6711e154
Source dataset
uspto-grants-2013_05
Patent number
US08445692B2

Reaction notes

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