Hydrochloric Acid → N-(2,6-dichloro-4-cyanophenyl)acetamide

HRID 917559

Reaction equation

HRID 917559 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:11])[C:9]=1[NH2:10])[C:5]#[N:6].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:22](Cl)(=[O:24])[CH3:23].Cl>C1COCC1.O.C(Cl)Cl>[C:22]([NH:10][C:9]1[C:2]([Cl:1])=[CH:3][C:4]([C:5]#[N:6])=[CH:7][C:8]=1[Cl:11])(=[O:24])[CH3:23]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 5227064-Amino-3,5-dichlorobenzonitrileHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 2735977N-(2,6-dichloro-4-cyanophenyl)acetamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Step AT1. To a solution of 3,5-dichloro-4-amino-benzonitrile (187 mg, 1 mmol) in 4 mL of THF at room temperature was added 2.2 mL of 1.0 M NaHMDS in THF. The resulting reaction mixture was stirred at room temperature for 30 min., at which time acetyl chloride (3.1 mmol) was added. DCM (100 mL) and water (100 mL) were added to the reaction mixture after being stirred overnight, followed by the addition of 5 mL of 1.4 N HCl aqueous solution. Layers were separated and the aqueous layer was extracted with DCM (2×100 mL). The extracts were combined and solvents were evaporated in vacuo. The residue was purified by HPLC to give 4-acetamido-3,5-dichloro-benzonitrile.

Workup

  1. customThe resulting reaction mixture
  2. additionwas added
  3. customLayers were separated
  4. extractionthe aqueous layer was extracted with DCM (2×100 mL)
  5. customsolvents were evaporated in vacuo
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-4fba62e91f914327bb951721dd6a0152
Source dataset
uspto-grants-2007_09
Patent number
US07273882B2

Linked notes

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