Methyl iodide → HCID 13473423, compound

HRID 260186Notes

Reaction equation

HRID 260186 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-07ab03f67d36421b8b43505453671780
Source dataset
uspto-grants-1996_06
Patent number
US05525727

Reaction notes

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