Pyridine → HCID 3573095, compound

HRID 2224091Notes

Reaction equation

HRID 2224091 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].N1C=CC=CC=1.[C:17](Cl)(=[O:21])[CH2:18][CH2:19][CH3:20]>C(Cl)Cl>[C:17]([NH:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:21])[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 3573095HCID 3573095, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a flame dried flask equipped with stir bar was added methyl 3-aminothiophene-2-carboxylate (2.06 g, 13.1 mmol) and anhydrous methylene chloride (10.0 mL). The resulting solution was cooled to 0° C., and treated successively with pyridine (1.11 mL, 13.7 mmol) and butyryl chloride (1.44 mL, 13.7 mmol) while stirring under N2. The ice bath was removed, and the reaction warmed to 25° C. and stirred 3 h. The reaction was then poured into 1N HCl and extracted with methylene chloride. The combined organics were dried over magnesium sulfate, filtered and concentrated to provide methyl 3-(butyrylamino)thiophene-2-carboxylate (1-2). MS 228 found, 227.3 required.

Workup

  1. customTo a flame dried flask
  2. customequipped
  3. stirringwhile stirring under N2
  4. customThe ice bath was removed
  5. temperaturethe reaction warmed to 25° C.
  6. stirringstirred 3 h
  7. additionThe reaction was then poured into 1N HCl
  8. extractionextracted with methylene chloride
  9. dry with materialThe combined organics were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-e389dc6669904a4e9b8feb59ea52fb0a
Source dataset
uspto-grants-2008_05
Patent number
US07378411B2

Reaction notes

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