Formamide → HCID 68110182, compound

HRID 525060Notes

Reaction equation

HRID 525060 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][C:9]([CH3:11])([CH3:10])[C:4]=2[C:3]=1[C:12]([O:14]CC)=O.O.[CH:18]([NH2:20])=O>>[CH3:10][C:9]1([CH3:11])[C:4]2[C:3]3[C:12](=[O:14])[NH:20][CH:18]=[N:1][C:2]=3[S:6][C:5]=2[CH2:7][CH2:8]1

Participants

4

Reactant 3

HCID 713FormamideHCID 962WaterHCID 68726389HCID 68726389, compound

Product 1

HCID 68110182HCID 68110182, compoundYield 75%

Conditions

Temperature
180 °C

Procedure

Ethyl 2-amino-4,4-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate (2.3 g, 9.9 mmol, 1 equiv.) was dissolved in formamide (12 mL). The mixture was stirred for 1 hour at 180° C. Then water (50 mL) was added and the product extracted with ethyl acetate (50 mL*3). The organic layer was washed with water (100 mL*2) and brine (100 mL), dried by sodium sulfate and filtered. The organic layer was concentrated and the residue purified by column chromatography (hexane:ethyl acetate=6:5) to give the desired product (1.57 g, 75%) as a yellow solid. MS: m/z 221 (M+H)+.

Workup

  1. extractionthe product extracted with ethyl acetate (50 mL*3)
  2. washThe organic layer was washed with water (100 mL*2) and brine (100 mL)
  3. dry with materialdried by sodium sulfate
  4. filtrationfiltered
  5. concentrationThe organic layer was concentrated
  6. customthe residue purified by column chromatography (hexane:ethyl acetate=6:5)

Sources & evidence

ORD record
ord-951becd6bc6e4ddeaef08797d7f02126
Source dataset
uspto-grants-2016_05
Patent number
US09340554B2

Reaction notes

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