1-Methylpyrrole → HCID 11040770, compound

HRID 1388938Notes

Reaction equation

HRID 1388938 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[C:12]([S:3][C:1]#[N:2])=[CH:11][CH:10]=[CH:9]1

Participants

5

Reactant 3

HCID 73041-MethylpyrroleHCID 24408BromineHCID 516872Potassium thiocyanate

Product 1

HCID 11040770HCID 11040770, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-78 °C

Procedure

Under nitrogen atmosphere, to a mixture of 25.08 g of KSCN (0.125 mole) in 60 ml dry methanol chilled to -78° C. was added dropwise 20 g of Br2 (in 40 ml methanol). The resulting yellow solution was stirred for 5-10 minutes and 10.1 g (0.125 mole) of the 1-methylpyrrole added in one portion. The mixture was allowed to warm to ambient temperature and stirred for one hour. The mixture was poured into 600 ml of ice-water, extracted 2 times with 300 ml CH2Cl2. The CH2Cl2 extract was dried and concentrated to 16.1 g (90% yield) of 1-methyl-5-cyanothiopyrrole.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred for one hour
  3. extractionextracted 2 times with 300 ml CH2Cl2
  4. extractionThe CH2Cl2 extract
  5. customwas dried

Sources & evidence

ORD record
ord-b6bf786f4ef54ebf90c1acaa68afbdb0
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Reaction notes

Loading…