Triethylamine → HCID 178514511, compound

HRID 626656Notes

Reaction equation

HRID 626656 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[CH:10]=O)=[N+:2]=[N-:3].[Cl:12][C:13]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:14]=1[NH2:15].C(N(CC)CC)C>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[N:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1/[CH:10]=[N:15]/[C:14]1[C:13]([Cl:12])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:20])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 118462,6-DichloroanilineHCID 866970374-Azidopyridine-3-carbaldehyde

Product 1

HCID 178514511HCID 178514511, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Titanium tetrachloride (1M, 4.3 mL, 4.3 mmol) was added to a cooled (0° C.) mixture of 4-azidopyridine-3-carbaldehyde (1.06 g, 7.2 mmol), 2,6-dichloroaniline (1.17 g, 7.2 mmol) and triethylamine (3.0 mL, 21.6 mmol) in DCM (24 mL) under nitrogen. The resultant mixture was stirred for 3 hours at 0° C. before warming to room temperature and stirring for a further 3 hours. The reaction mixture was 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 a yellow solid. This crude material was employed in the next step without further purification or analysis.

Workup

  1. temperaturea cooled
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. filtrationfiltered though a pad of Celite®
  4. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-04f32f1d2a854a37b7eeb947c4abed8c
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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