Triethylamine → HCID 178509963, compound

HRID 626687Notes

Reaction equation

HRID 626687 reaction equation
C(N(CC)CC)C.[N:8]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[CH:17]=O)=[N+:9]=[N-:10].[NH2:19][C:20]1[C:27]([Cl:28])=[CH:26][C:23]([C:24]#[N:25])=[CH:22][C:21]=1[Cl:29]>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[N:8]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1/[CH:17]=[N:19]/[C:20]1[C:21]([Cl:29])=[CH:22][C:23]([C:24]#[N:25])=[CH:26][C:27]=1[Cl:28])=[N+:9]=[N-:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5227064-Amino-3,5-dichlorobenzonitrileHCID 866970374-Azidopyridine-3-carbaldehyde

Product 1

HCID 178509963HCID 178509963, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (8.9 mL, 64.2 mmol) was added to a cooled (0° C.) mixture of 4-azidopyridine-3-carbaldehyde (3.2 g, 21.4 mmol) and 4-amino-3,5-dichlorobenzonitrile (4.0 g, 21.4 mmol) in DCM (80 mL) under nitrogen. Titanium tetrachloride (1M, 12.8 mL, 12.8 mmol) was added and then the reaction mixture was stirred for 1 hour at 0° C. After warming to room temperature, the reaction was stirred for an additional 2 h and then concentrated under reduced pressure. The residue was suspended in toluene and filtered though a pad of Celite®. The filtrate was concentrated to dryness under reduced pressure to afford the title compound as an orange solid. This crude material was employed in the next step without further purification or analysis.

Workup

  1. temperaturea cooled
  2. temperatureAfter warming to room temperature
  3. stirringthe reaction was stirred for an additional 2 h
  4. concentrationconcentrated under reduced pressure
  5. filtrationfiltered though a pad of Celite®
  6. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-fd679328e6d44839be6152edf94042d0
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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