Indole → HCID 19602310, compound

HRID 1604234Notes

Reaction equation

HRID 1604234 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[CH2:12]([N:14]=[C:15]=[O:16])[CH3:13]>C1COCC1>[CH2:12]([NH:14][C:15]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1)=[O:16])[CH3:13]

Participants

5

Reactant 3

HCID 798IndoleHCID 8022Ethyl isocyanateHCID 24758Sodium hydride

Product 1

HCID 19602310HCID 19602310, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (0.9 g, 37.5 mmol) was added in portions to a 0° C. cooled solution of indole (2.93 g, 25 mmol) in THF (100 mL). After 30 min, ethyl isocyanate (1.78 g, 25 mmol) was added dropwise. The reaction mixture was stirred at RT overnight, then was quenched with 25% citric acid in water (50 mL) and extracted with ethyl acetate (3 X). These organic extracts were combined, dried (MgSo4), and recrystallized from ether/hexanes to afford 1.3 g of N-(ethylaminocarbonyl)indole as a tan solid, a 28% yield. m.p. 71-73° C.

Workup

  1. customwas quenched with 25% citric acid in water (50 mL)
  2. extractionextracted with ethyl acetate (3 X)
  3. customdried (MgSo4)
  4. customrecrystallized from ether/hexanes

Sources & evidence

ORD record
ord-70b1c79bf5e3428892b69ac7e905d56c
Source dataset
uspto-grants-1999_11
Patent number
US05994270

Reaction notes

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