Sodium → HCID 67262655, compound

HRID 76814Notes

Reaction equation

HRID 76814 reaction equation
[Na].[CH3:2][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:13])([CH3:12])/[C:4]/1=[CH:14]/[C:15]([NH:17]C(=O)C1C=CC=CC=1)=S>CO>[CH3:2][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:13])([CH3:12])[CH:4]1[CH2:14][C:15]#[N:17]

Participants

4

Reactant 2

HCID 5360545Sodium2×HCID 15124031HCID 15124031, compound

Product 1

HCID 67262655HCID 67262655, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 500-mL one-necked flask was equipped with a magnetic stir bar and a reflux condenser. 200 mL of methanol were added to the flask, sodium (3.0 g, 0.13 mole) was added to the methanol as small pieces (approximately 0.5 g). After the sodium dissolved, N-[(2Z)-2-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)ethanethioyl]-benzamide (19.0 g, 0.056 mole) was added to the flask and the reaction mixture was heated at reflux with stirring for 2 hours. The reaction mixture was cooled to room temperature and the methanol was evaporated using a rotary evaporator. The residue was treated with 200 mL of water and extracted with dichloromethane (3×100 mL). Combined organic extracts were dried over magnesium sulfate and the solvent was evaporated on a rotary evaporator. The red solid was recrystallized from methanol-water (7:3) to give slightly red crystals. The yield was 4.5 g (40% of theory). Mp=74-76° C.

Workup

  1. customA 500-mL one-necked flask was equipped with a magnetic stir bar and a reflux condenser
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux
  4. customthe methanol was evaporated
  5. customa rotary evaporator
  6. additionThe residue was treated with 200 mL of water
  7. extractionextracted with dichloromethane (3×100 mL)
  8. dry with materialCombined organic extracts were dried over magnesium sulfate
  9. customthe solvent was evaporated on a rotary evaporator
  10. customThe red solid was recrystallized from methanol-water (7:3)
  11. customto give slightly red crystals

Sources & evidence

ORD record
ord-bd1f7daeeed5474597fef49cafbd60a9
Source dataset
uspto-grants-2014_09
Patent number
US08835632B2

Reaction notes

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