Triethylamine → HCID 4927441, compound

HRID 1191026Notes

Reaction equation

HRID 1191026 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][C:2]([CH3:7])([CH3:6])[C:3]([NH:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 133964-AminobenzonitrileHCID 62493Pivaloyl chloride

Product 1

HCID 4927441HCID 4927441, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add dropwise trimethylacetyl chloride (3.3 mL, 27 mmol) to a mixture of 4-aminobenzonitrile (2.92 g, 24.7 mmol) and triethylamine (3.8 mL, 27 mmol) in anhydrous DCM (25 mL) at 0° C. Stir the mixture to room temperature overnight. Partition the reaction mixture between DCM (500 mL) and water (250 mL) and extract the aqueous phase with DCM (250 mL). Wash the combined organic extracts with water (3×250 mL), dry over Na2SO4, filter and concentrate in vacuo to obtain the desired intermediate (5 g, 100%). MS (ES+) m/z: 203.2 (M+H)+.

Workup

  1. customPartition the reaction mixture between DCM (500 mL) and water (250 mL)
  2. extractionextract the aqueous phase with DCM (250 mL)
  3. washWash the combined organic extracts with water (3×250 mL)
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-9c92c74e60bb449a805b78e3018ccfde
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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