Methyl iodide → HCID 13473425, compound

HRID 2081986Notes

Reaction equation

HRID 2081986 reaction equation
[C:1]([O:7][C:8]1[CH:9]=[C:10]([CH2:21][CH2:22][NH:23][C:24]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[O:25])[CH:11]=[CH:12][C:13]=1[O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:32][I:33]>CC(C)=O>[I-:33].[CH3:32][N+:28]1[CH:29]=[CH:30][CH:31]=[C:26]([C:24](=[O:25])[NH:23][CH2:22][CH2:21][C:10]2[CH:11]=[CH:12][C:13]([O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[C:8]([O:7][C:1](=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5])[CH:9]=2)[CH:27]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 134734203-{N-[beta-(3,4-Dipivalyloxyphenyl)ethyl]}carbamoylpyridine

Product 1

HCID 13473425HCID 13473425, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5.0 g (11.7 mmol) of compound 8c in 20 ml of acetone, 3.3 g (23.4 mmol) of methyl iodide were added and the mixture was refluxed under stirring for 6 hrs, then cooled. The orange crystalline solid which separated was filtered, washed with ether and crystallized for acetone/ether. Yield, 5.6 g (85%), m.p. 163°-165° C. U.V. (buffer pH 7.4) 270, 215 nm. NMR (DMSO-d6) δ 7.68-7.06 (ms, 7H, C5N4N+ +C6H3 +NH), 4.56 (s, 3H, --N+ --CH3), 3.42 (q, 2H, J=7 Hz, --N--CH2), 3.19 (t, 2H, J=7 Hz, CH2), 1.32 (s, 18H, 2 --C(CH3)3). Anal. Calcd for C25H33IN2O5 : C, 52.82 ; H, 5.85; N, 4.92. Found: C, 52.76; H, 5.87; N, 4.90.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturecooled
  3. customThe orange crystalline solid which separated
  4. filtrationwas filtered
  5. washwashed with ether
  6. customcrystallized for acetone/ether
  7. customYield

Sources & evidence

ORD record
ord-a0fc272aecce4683997d9e8e1f070ff2
Source dataset
uspto-grants-1993_02
Patent number
US05187158

Reaction notes

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