Sodium hydride → 1-[2-(N-phenylcarbamoyl)ethyl]-3-(1-imidazolylmethyl)indole

HRID 1680486Notes

Reaction equation

HRID 1680486 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1.[H-].[Na+].Cl[CH2:19][CH2:20][C:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22]>CN(C)C=O>[C:24]1([NH:23][C:21]([CH2:20][CH2:19][N:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7]([CH2:6][C:2]3[NH:3][CH:4]=[CH:5][N:1]=3)=[CH:8]2)=[O:22])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2404043-chloro-N-phenylpropanamideHCID 538640233-(1-Imidazolylmethyl) indole

Product 1

HCID 705760211-[2-(N-phenylcarbamoyl)ethyl]-3-(1-imidazolylmethyl)indoleYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-(1-Imidazolylmethyl)indole (1.97 g) was dissolved in dry N,N-dimethylformamide (50 ml) and the solution was cooled to °C. Sodium hydride (0.55 g of 50% dispersion in oil) was added portionwise with stirring and the mixture was stirred at 0° C. for 30 minutes. A solution of 3-chloropropionanilide (1.83 g) in dry N,N-dimethylformamide was added dropwise with stirring and the resulting mixture was stirred at 0° C. for 2 hours followed by 18 hours at room temperature. The mixture was evaporated and water was added to the residue. The solid product was filtered off, washed with chloroform to remove impurity and crystallised from methanol to give 1-[2-(N-phenylcarbamoyl)ethyl]-3-(1-imidazolylmethyl)indole (1.20 g), m.p. 254°-255° C. Found: C, 73.14; H, 5.82; N, 15.88. C21H20N4O requires: C, 73.23; H, 5.85; N, 16.27%.

Workup

  1. temperaturethe solution was cooled to °C
  2. stirringthe mixture was stirred at 0° C. for 30 minutes
  3. stirringwith stirring
  4. stirringthe resulting mixture was stirred at 0° C. for 2 hours
  5. customThe mixture was evaporated
  6. additionwater was added to the residue
  7. filtrationThe solid product was filtered off
  8. washwashed with chloroform
  9. customto remove impurity
  10. customcrystallised from methanol

Sources & evidence

ORD record
ord-a369d577fb4c49b1bbd2fc3e45f6e742
Source dataset
uspto-grants-1981_06
Patent number
US04273782

Reaction notes

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