Methyl iodide → Ethanol

HRID 1110341Notes

Reaction equation

HRID 1110341 reaction equation
N[C:2]1[S:3][C:4]2[CH:10]=[C:9]([S:11][C:12]#N)[C:8]([S:14][CH3:15])=[CH:7][C:5]=2[N:6]=1.[OH-:16].[Na+].[BH4-].[Na+].IC>C(O)C.O>[CH3:2][S:3][C:4]1[CH:10]=[C:9]([S:11][CH3:12])[C:8]([S:14][CH3:15])=[CH:7][C:5]=1[NH2:6].[CH2:10]([OH:16])[CH3:4]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 22155113HCID 22155113, compound

Product 2

HCID 702EthanolYield 33%HCID 22155111HCID 22155111, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2,4,5-Trimethylthioaniline was prepared by combining 2-amino-5-methylthio-6-thiocyanatobenzothiazole (220 g, 0.87 mol) with 1.2 L of water, 1.0 L of 50% sodium hydroxide solution, and sodium borohydride (40 g, 1.06 mol) in a 5 L, 3-necked flask. The mixture was stirred with a mechanical stirrer and refluxed under a nitrogen atmosphere for 15 hr. The mixture was cooled to room temperature and ethanol (800 mL) was added followed by addition of iodomethane (300 g, 2.11 mole). The solution was collected and dried. The product was recrystallized from ethanol (66 g, 33% yield).

Workup

  1. temperaturerefluxed under a nitrogen atmosphere for 15 hr
  2. customThe solution was collected
  3. customdried

Sources & evidence

ORD record
ord-0fcef46ffd8f402b9fcce3d2aac248cf
Source dataset
uspto-grants-1990_12
Patent number
US04975362

Reaction notes

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