Ethanol → HCID 16767826, compound

HRID 1066870Notes

Reaction equation

HRID 1066870 reaction equation
C(O)C.[NH2:4][C:5]1[CH:9]=[CH:8][S:7][C:6]=1[C:10]([O:12]C)=O.[CH2:14]([N:17]=[C:18]=[S:19])[CH2:15][CH3:16]>C(N(CC)CC)C>[CH2:14]([N:17]1[C:10](=[O:12])[C:6]2[S:7][CH:8]=[CH:9][C:5]=2[NH:4][C:18]1=[S:19])[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 702EthanolHCID 69403Propyl IsothiocyanateHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 16767826HCID 16767826, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a suspension of 150 mL of ethanol containing 9.5 g of methyl 3-amino-2-thiophenecarboxylate was added dropwise 9.3 mL of n-propyl isothiocyanate with stirring. To this reaction mixture was added 12.64 mL of triethylamine. The reaction mixture was heated at reflux for 3 h, allowed to cool to room temperature and then stirred for approximately 24 h. The mixture was then heated at reflux for an additional 32 h, cooled to approximately 5° C. and filtered to obtain 5.5 g of the title compound of Step A as an off-white solid melting at 246-249° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. stirringstirred for approximately 24 h
  4. temperatureThe mixture was then heated
  5. temperatureat reflux for an additional 32 h
  6. temperaturecooled to approximately 5° C.
  7. filtrationfiltered

Sources & evidence

ORD record
ord-6395cb11c30d4fac937a122e43558ff5
Source dataset
uspto-grants-2001_06
Patent number
US06245770B1

Reaction notes

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