Methyl iodide → HCID 135741846, compound

HRID 732932Notes

Reaction equation

HRID 732932 reaction equation
[OH:1][CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:3][N:4]1[C:8]2[NH:9][C:10](=[S:14])[NH:11][C:12](=[O:13])[C:7]=2[CH:6]=[N:5]1.[CH3:21]I>C1COCC1>[OH:1][CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([S:14][CH3:21])[NH:11][C:12](=[O:13])[C:7]=2[CH:6]=[N:5]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 136383527HCID 136383527, compound

Product 1

HCID 135741846HCID 135741846, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7 (2.88 g, 10 mmol) and methyl iodide (7.10 g, 50 mmol) in anhydrous THF (20 mL) was refluxed for 12 h. The solvent and the excess of methyl iodide were removed by distillation under reduced pressure; the oil residue crystallized by adding CHCl3 (10 mL) and was purified by recrystallization with absolute ethanol to give 8a (2.17 g, 72%) as a white solid; mp 208-209° C. 1H NMR: δ 2.51 (s, 3H, CH3), 4.27-4.50 (m, 2H, CH2N), 5.04-5.18 (m, 1H, CHO), 5.68 (d, 1H, OH, disappears with D2O), 7.20-7.42 (m, 5H Ar), 7.97 (s, 1H, H-3). IR cm−1: 3544 (NH), 3450-3350 (OH), 1678 (CO). Anal. (C14H14N4O2S) C, H, N, S.

Workup

  1. customThe solvent and the excess of methyl iodide were removed by distillation under reduced pressure
  2. customthe oil residue crystallized
  3. additionby adding CHCl3 (10 mL)
  4. customwas purified by recrystallization with absolute ethanol

Sources & evidence

ORD record
ord-42cbe7e89d574d32a49ff7bc652e5f7f
Source dataset
uspto-grants-2009_09
Patent number
US07589086B2

Reaction notes

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