Dichloromethane → HCID 16093753, compound

HRID 515915Notes

Reaction equation

HRID 515915 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[CH:10]=[CH:9][N:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:7]=1.[N:21]#[C:22]Br.ClCCl>ClCCCl.O>[CH3:5][C:6]1[CH:10]=[CH:9][N:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:12])=[O:13])[C:7]=1[C:22]#[N:21]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10476Cyanogen Bromide2×HCID 6451240Aluminum(III) ChlorideHCID 14962127HCID 14962127, compound

Product 1

HCID 16093753HCID 16093753, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Aluminium chloride (19.4 g, 0.15 mol) is added all at once to a solution of 3-methyl-1-(4-methylbenzenesulphonyl)-1H-pyrrole (13.0 g, 55.3 mmol) in 1,2-dichloroethane (230 mL) at ambient temperature. After stirring for 20 minutes, cyanogen bromide (11.11 g, 0.10 mol) is added in portions over a period of 20 minutes. After 4.5 hours, an additional amount of cyanogen bromide (1.94 g, 18.3 mmol) is added. After stirring for 17 hours at ambient temperature, the reaction mixture is poured slowly into a mixture of dichloromethane (300 mL) and water (600 mL) cooled to 0° C. The resulting mixture is stirred for 1 hour. Subsequently the phases are separated and the aqueous phase is extracted with dichloromethane (3×150 mL). The combined organic phases are washed with water (2×150 mL) and brine (150 mL). The organic phase is dried over Na2SO4, filtered and concentrated in vacuo to obtain the expected compound in the form of a solid.

Workup

  1. waitAfter 4.5 hours
  2. stirringAfter stirring for 17 hours at ambient temperature
  3. stirringThe resulting mixture is stirred for 1 hour
  4. customSubsequently the phases are separated
  5. extractionthe aqueous phase is extracted with dichloromethane (3×150 mL)
  6. washThe combined organic phases are washed with water (2×150 mL) and brine (150 mL)
  7. dry with materialThe organic phase is dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6cd9a5bb4e74e37b8ede942b628e1ec
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

Loading…