1-Methylpyrrole → HCID 11040770, compound

HRID 1981063Notes

Reaction equation

HRID 1981063 reaction equation
[C:1]([S-:3])#[N:2].[K+].BrBr.[CH3:7][N:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1>CO>[CH3:7][N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[S:3][C:1]#[N:2]

Participants

5

Reactant 3

HCID 73041-MethylpyrroleHCID 24408BromineHCID 516872Potassium thiocyanate

Product 1

HCID 11040770HCID 11040770, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Under nitrogen atmosphere, to a mixture of 25 g of KSCN in 60 ml of dry methanol at -78° C. was added 20 g of Br2 dissolved in 45 ml of methanol. The resulting yellow solution was stirred for 5-10 minutes and 10.1 g of 1-methylpyrrole added in one portion. The mixture was allowed to warm to room temperature and stirred for an additional hour. The mixture was poured into 600 ml of ice-water and extracted twice with 200 ml of methylene chloride. The methylene chloride layer was washed, dried and then concentrated to yield 16.1 g of light yellow oil that turns reddish upon standing.

Workup

  1. stirringstirred for an additional hour
  2. extractionextracted twice with 200 ml of methylene chloride
  3. washThe methylene chloride layer was washed
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4cc64627f7374a928d113d658c6730f5
Source dataset
uspto-grants-1985_04
Patent number
US04511724

Reaction notes

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