Methyl iodide → HCID 13473423, compound

HRID 1638851Notes

Reaction equation

HRID 1638851 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:15][CH2:16][NH:17][C:18]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[O:19])[CH:8]=[CH:9][C:10]=1[O:11][C:12](=[O:14])[CH3:13])(=[O:3])[CH3:2].[C:26](OC1C=C(CCNC(C2C=NC=CC=2)=O)C=CC=1OC(=O)C(C)(C)C)(=O)C(C)(C)C.C[I:58]>CO>[I-:58].[CH3:26][N+:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:18](=[O:19])[NH:17][CH2:16][CH2:15][C:7]2[CH:8]=[CH:9][C:10]([O:11][C:12](=[O:14])[CH3:13])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[CH:21]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 134734193-{N-[beta-(3,4-diacetoxyphenyl)ethyl]}carbamoylpyridineHCID 134734203-{N-[beta-(3,4-Dipivalyloxyphenyl)ethyl]}carbamoylpyridine

Product 1

HCID 13473423HCID 13473423, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.71 g (5 mmol) of 3-{N-[β-(3,4-diacetoxyphenyl)ethyl]}carbamoylpyridine (prepared like compound 8c), 1.41 g (10 mmol) of methyl iodide were added and the mixture was refluxed overnight under stirring. The acetone solution was then decanted from the insoluble oily residue. Ether was added to the acetone solution and the solid which separated was crystallized from acetone/ether. Yield, 1.9 g (78%) of yellow crystalline needles, m.p. 171°-173° C. U.V. (methanol) 215, 265 nm; NMR (D2O) δ 8.86-7.63 (ms, 4H, C5H4N+), 6.66 (bs, 3H, C6H3), 4.4 (s, 3H, --N+ --CH3), 3.50 (t, 2H, --N--CH2), 3.03 (t, 2H, CH2), 2.21 (bs, 6H, 2 COCH3). Anal. Calcd for C19H21IN2O5 : C, 47.12; H, 4.37; N, 5.78. Found: C, 47.23; H, 4.38; N, 5.78.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe acetone solution was then decanted from the insoluble oily residue
  3. additionEther was added to the acetone solution
  4. customthe solid which separated
  5. customwas crystallized from acetone/ether
  6. customYield

Sources & evidence

ORD record
ord-32e207aa9f514efeb384ff0c511d587a
Source dataset
uspto-grants-1989_11
Patent number
US04880921

Reaction notes

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