Methyl iodide → 31401-33-9

HRID 2088238Notes

Reaction equation

HRID 2088238 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[N:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[C:20](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[N:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27534374-(4-Butylphenylazo)phenol

Product 1

HCID 275341631401-33-9

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
45 °C

Procedure

All chemicals were obtained from Sigma-Aldrich Chemical Co. unless otherwise noted. One eq. of 4-butyl-4′-hydroxyazobenzene (obtained from Beam Corp.) and 1.1 eq. potassium carbonate were dissolved in acetone and degassed with argon. Iodomethane (2.5 eq) in acetone was degassed and added drop-wise to the stirred mixture. The mixture was heated to 45° C. and stirred overnight. The progress of the reaction was monitored by thin-layer chromatography (TLC); 12 h was usually sufficient for complete methylation. The hot reaction mixture was then filtered to remove the precipitated potassium iodide. The filtrate was collected and the solvent removed in vacuo. The solid residue was re-dissolved in chloroform and then insoluble salts were removed by filtration. The filtrate was washed with water, and the organic layer was separated and dried over magnesium sulfate. Removing the solvent in vacuo afforded a solid that contained the desired product (“BMAB”) containing a small amount of un-reacted starting material 4-butyl-4′-hydroxyazobenzene. Recrystallization from methanol at −68° C. afforded pure crystals of BMAB that were collected by filtration. (K 35 N 45 I) 1H NMR 200 MHz δ ppm=0.94 (t, 3H), 1.18 (q, 2H), 1.66 (q, 2H), 2.66 (t, 2H), 3.86 (s, 2H), 7.0 (d, 2H), 7.26 (d, 2H), 7.82 (d, 2H), 7.88 (d, 2H).

Workup

  1. customdegassed with argon
  2. additionadded drop-wise to the stirred mixture
  3. custom12 h
  4. filtrationThe hot reaction mixture was then filtered
  5. customto remove the precipitated potassium iodide
  6. customThe filtrate was collected
  7. customthe solvent removed in vacuo
  8. dissolutionThe solid residue was re-dissolved in chloroform
  9. custominsoluble salts were removed by filtration
  10. washThe filtrate was washed with water
  11. customthe organic layer was separated
  12. dry with materialdried over magnesium sulfate
  13. customRemoving the solvent in vacuo
  14. customafforded a solid

Sources & evidence

ORD record
ord-987d56cac95d446c81b289b7044a9ade
Source dataset
uspto-grants-2013_05
Patent number
US08435333B2

Reaction notes

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