2,6-Dichloroaniline → HCID 178512060, compound

HRID 1466411Notes

Reaction equation

HRID 1466411 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].C[Al](C)C.[Br:14][C:15]1[S:19][C:18]([C:20]#[N:21])=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[Br:14][C:15]1[S:19][C:18]([C:20]([NH:4][C:3]2[C:2]([Cl:1])=[CH:8][CH:7]=[CH:6][C:5]=2[Cl:9])=[NH:21])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 118462,6-DichloroanilineHCID 35950595-Bromothiophene-2-carbonitrileHCID 16682925Trimethylaluminum

Product 1

HCID 178512060HCID 178512060, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 2,6-dichloroaniline (1.75 g, 10.8 mmol) in toluene (25 mL, anhyd) was added dropwise a 2.0M solution of trimethylaluminum in toluene (8.0 mL, 16 mmol). After 90 min the reaction mixture was charged with a solution of 5-bromothiophene-2-carbonitrile (3.00 g, 16 mmol) in toluene (20 mL, anhyd) and then heated at 90° C. After 5 h the reaction mixture was allowed to cool to ambient temperature and quenched by addition to a stirred slurry of silica (25 g) in 3:1 CHCl3/MeOH (100 mL). After 30 min the resulting mixture was filtered and the solids rinsed with MeOH and DCM. The combined filtrates were concentrated to afford the title compound (3.9 g, quant) as a pale yellow solid, which was used in the next step without purification. GC-MS (EI): 348, 350, 352.

Workup

  1. temperatureto cool to ambient temperature
  2. customquenched by addition to a stirred slurry of silica (25 g) in 3:1 CHCl3/MeOH (100 mL)
  3. filtrationAfter 30 min the resulting mixture was filtered
  4. washthe solids rinsed with MeOH and DCM
  5. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-7b1efc9416a54534a8445b466498df7c
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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