Methyl iodide → HCID 19374904, compound

HRID 128695Notes

Reaction equation

HRID 128695 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11]1[N:12]=[C:13]([N:17]([CH:21]([CH:27]2[CH2:29][CH2:28]2)[C:22]2[N:23]=[CH:24][NH:25][CH:26]=2)[CH2:18][CH2:19][CH3:20])[S:14][C:15]=1[CH3:16].[CH3:30]I>CC(C)=O.ClCCl>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11]1[N:12]=[C:13]([N:17]([CH:21]([CH:27]2[CH2:29][CH2:28]2)[C:22]2[N:23]=[CH:24][N:25]([CH3:30])[CH:26]=2)[CH2:18][CH2:19][CH3:20])[S:14][C:15]=1[CH3:16]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178456836HCID 178456836, compound

Product 1

HCID 19374904HCID 19374904, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

Add 570 mg of powdered potassium hydroxide to 856 mg of the compound of Example 42 dissolved in 10 ml of acetone. Stir for 5 minutes and then add 0.14 ml of methyl iodide. After 15 minutes at room temperature, dilute the reaction mixture in 100 ml of dichloromethane, and then wash with water and with water saturated with sodium chloride. Dry the organic phase over sodium sulphate, evaporate to dryness and then subject the residue to chromatography on a silica column, using a mixture of cyclohexane and ethyl acetate (1:1 V/V) as eluent.

Workup

  1. waitAfter 15 minutes at room temperature
  2. washwash with water and with water saturated with sodium chloride
  3. dry with materialDry the organic phase over sodium sulphate
  4. customevaporate to dryness
  5. additiona mixture of cyclohexane and ethyl acetate (1:1 V/V) as eluent

Sources & evidence

ORD record
ord-8903b1d6f891402c8697dcb22deb2fa3
Source dataset
uspto-grants-1995_11
Patent number
US05464847

Reaction notes

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