Methyl iodide → HCID 19020561, compound

HRID 1109544Notes

Reaction equation

HRID 1109544 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[CH:20]=[CH:19][C:18]2[S:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:21]([CH3:28])[CH2:22][N:23]3[CH2:27][CH:26]=[CH:25][CH2:24]3)[C:9]=2[CH:8]=1)=[O:6])[CH:2]=[CH2:3].[CH3:29][I:30]>CC(C)=O>[I-:30].[CH2:1]([NH:4][C:5]([C:7]1[CH:20]=[CH:19][C:18]2[S:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:21]([CH3:28])[CH2:22][N+:23]3([CH3:29])[CH2:27][CH:26]=[CH:25][CH2:24]3)[C:9]=2[CH:8]=1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 20074870HCID 20074870, compound

Product 1

HCID 19020561HCID 19020561, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of N-allyl-10-[1-(2,5-dihydro-1-pyrrolyl)-2-propyl]-2-phenothiazinecarboxamide, L series (1.1 g), and methyl iodide (0.4 g) in acetone (10 cc) is stirred for 3 days at a temperature in the region of 20° C. and then concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 45° C. The residue is purified by chromatography on a column (height: 30 cm; diameter: 3 cm) of silica gel (0.04-0.063 mm) under a slight excess pressure of nitrogen (40 kPa), eluting successively with a mixture (300 cc) of ethyl acetate and methanol (90:10 by volume) and then with a mixture (500 cc) of ethyl acetate and methanol (80:20 by volume) and collecting 40-cc fractions. Fractions 5 to 15 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. and the residue is taken up with stirring for 30 minutes in isopropyl ether (40 cc). The suspension is filtered and the solid is washed with isopropyl ether (2×5 cc), drained and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C. 1-[2-(2-Allylcarbamoyl-10-pheno-thiazinyl)propyl]-1-methyl-2,5-dihydropyrrolium iodide, L series (0.66 g), is thereby obtained in the form of a yellow powder, m.p. about 170° C.

Workup

  1. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 45° C
  2. customThe residue is purified by chromatography on a column (height: 30 cm; diameter: 3 cm) of silica gel (0.04-0.063 mm) under a slight excess pressure of nitrogen (40 kPa)
  3. washeluting successively with a mixture (300 cc) of ethyl acetate and methanol (90:10 by volume)
  4. customwith a mixture (500 cc) of ethyl acetate and methanol (80:20 by volume) and collecting 40-cc fractions
  5. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  6. filtrationThe suspension is filtered
  7. washthe solid is washed with isopropyl ether (2×5 cc)
  8. customdried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C

Sources & evidence

ORD record
ord-f48b0f30f4fb4784a7dfa169e052275c
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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