Hydrochloric Acid → HCID 19759318, compound

HRID 1586792Notes

Reaction equation

HRID 1586792 reaction equation
ClS([N:5]=[C:6]=O)(=O)=O.[Br:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[N:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1.CN(C)C=O.Cl>C(Cl)Cl>[Br:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[N:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:6]#[N:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 47151991-(2-bromo-4-methylphenyl)-1H-pyrrole

Product 1

HCID 19759318HCID 19759318, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

Chlorosulfonyl isocyanate (1.2 ml) in methylene chloride (12 ml) was added dropwise to a stirred solution of 1-(2-bromo-4-methylphenyl)pyrrole (2.5 g) in methylene chloride (25 ml) kept about -20° C. under nitrogen atmosphere. The reaction mixture was stirred at -20° C. for 30 minutes and at room temperature for 1.5 hours, and then was added dropwise dimethylformamide (1.7 ml) keeping at about -20° C. The reaction mixture was stirred at -20° C. for 30 minutes and at room temperature for an hour. To the reaction mixture was added 4N-hydrochloric acid at 0° C., and stirred at 0° C. for 30 minutes. The organic layer was washed with water and saturated sodium hydrogencarbonate solution, and dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography with a mixture of ethyl acetate and n-hexane (1:10) as eluent to give 1-(2-bromo-4-methylphenyl)pyrrole-2-carbonitrile (2.4 g).

Workup

  1. customkept about -20° C. under nitrogen atmosphere
  2. customkeeping at about -20° C
  3. stirringThe reaction mixture was stirred at -20° C. for 30 minutes and at room temperature for an hour
  4. stirringstirred at 0° C. for 30 minutes
  5. washThe organic layer was washed with water and saturated sodium hydrogencarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography with a mixture of ethyl acetate and n-hexane (1:10) as eluent

Sources & evidence

ORD record
ord-7bac87a50956444392fe82814ec5e823
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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