Methyl iodide → HCID 70539793, compound

HRID 1759441Notes

Reaction equation

HRID 1759441 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)=[O:21])=[CH:16][CH:15]=1)[C:12]#[N:13].[CH3:27]I.C[O-].[Na+]>C(Cl)Cl.O.CO.COCCOC>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][C:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)=[O:21])=[CH:16][CH:15]=1)([CH3:27])[C:12]#[N:13]

Participants

8

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 20532027HCID 20532027, compound

Product 1

HCID 70539793HCID 70539793, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Methanol (5 ml) and 1 ml of DME were added to 788 mg of alpha-(2-benzothiazolylthio)[p-(2-thienylcarbonyl)phenyl]acetonitrile, and the mixture was stirred in an argon atmosphere under ice cooling. Methyl iodide (0.20 ml) and 0.81 ml of a 2.7 M methanol solution of sodium methoxide were added. The mixture was stirred under ice cooling for 1 hour, and then at room temperature for 3.5 hours. Water (20 ml) and 30 ml of methylene chloride were added, and the insoluble matter was removed by filtration. The filtrate was shaken, and the organic layer was separated. The aqueous layer was extracted with 20 ml of methylene chloride twice. The organic layers were combined, washed with 20 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated by column chromatography (silica gel; methylene chloride) to afford 73 mg of alpha-(2-benzothiazolylthio)alpha-[p-(2-thienylcarbonyl)phenyl]propionitrile as colorless crystals.

Workup

  1. stirringThe mixture was stirred under ice cooling for 1 hour
  2. customthe insoluble matter was removed by filtration
  3. stirringThe filtrate was shaken
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with 20 ml of methylene chloride twice
  6. washwashed with 20 ml of water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was separated by column chromatography (silica gel; methylene chloride)

Sources & evidence

ORD record
ord-20a9cd3e0f7c41ebafc6db074fd8aeaa
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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