Acetone → HCID 14810902, compound

HRID 1710102Notes

Reaction equation

HRID 1710102 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]2[N:15](C3C=CN=CC=3)[N:14]=[CH:13][O:12]2)=[CH:3]1.C[I:23].[CH3:24][C:25]([CH3:27])=O>>[I-:23].[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[O:12][C:13]([C:25]3[CH:27]=[CH:3][N+:2]([CH3:10])=[CH:1][CH:24]=3)=[N:14][N:15]=2)=[CH:3]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 6328Methyl iodideHCID 23035465HCID 23035465, compound

Product 1

HCID 14810902HCID 14810902, compound

Procedure

4-[2-(1-methylindol-3-yl)-1,3,4-oxadiazol-3-yl]pyridine (50 mg) was dissolved in dry acetone (10 ml), methyl iodide (127 mg) was then added, and the resulting solution heated at reflux for twenty four hours under a dry nitrogen atmosphere. The solution was allowed to cool to room temperature and the yellow solid isolated by filtration. Recrystallisation from acetone afforded the title compound (70 mg); m.p. 290° C. (dec); Found: C, 47.85; H, 3.56; N, 13.12; C17N16N4O15I requires C, 47.79; H, 3.77; N, 13.11%; δH (360 MHz, DMSO-d6) 3.98 (3H, s, N--CH3), 4.43 (3H, s, +N--CH3), 7.38 (2H, brm, H-5,6), 7.68 (1H, brm, H-4), 8.24 (1H, brm, H-7), 8.49 (1H, s, H-2), 8.70 (2H, d, J=8.4 Hz, CH=CH--N), 9.18 (2H, d, J=8.4 Hz, CH=CH--N); m/z (M+ free base 60%,) 276 (60), 158 (100), 127 (20), 103 (10), 77 (10).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux for twenty four hours under a dry nitrogen atmosphere
  3. customthe yellow solid isolated by filtration
  4. customRecrystallisation from acetone

Sources & evidence

ORD record
ord-edf95eedb6ef409c970a14b2dafd57a8
Source dataset
uspto-grants-1990_08
Patent number
US04952587

Reaction notes

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