Triethylamine → HCID 178509964, compound

HRID 626706Notes

Reaction equation

HRID 626706 reaction equation
[N:1]([C:4]1[C:9]([Cl:10])=[CH:8][N:7]=[CH:6][C:5]=1[CH:11]=O)=[N+:2]=[N-:3].[NH2:13][C:14]1[C:21]([Cl:22])=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=1[Cl:23].C(N(CC)CC)C>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[N:1]([C:4]1[C:9]([Cl:10])=[CH:8][N:7]=[CH:6][C:5]=1/[CH:11]=[N:13]/[C:14]1[C:15]([Cl:23])=[CH:16][C:17]([C:18]#[N:19])=[CH:20][C:21]=1[Cl:22])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5227064-Amino-3,5-dichlorobenzonitrileHCID 866970494-Azido-5-chloropyridine-3-carbaldehyde

Product 1

HCID 178509964HCID 178509964, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 4-azido-5-chloropyridine-3-carbaldehyde (2.0 g, 10.95 mmol), 4-amino-3,5-dichlorobenzonitrile (2.05 g, 10.95 mmol) and triethylamine (4.6 mL, 6.57 mmol) in DCM (48 mL) was added titanium tetrachloride (1M in DCM, 6.6 mL, 6.57 mmol) dropwise over 10 minutes. The reaction mixture was stirred for 20 minutes, warmed to room temperature, and stirred for an additional 30 minutes. The resultant mixture was concentrated to dryness under reduced pressure to afford the title compound which was used without further purification.

Workup

  1. stirringstirred for an additional 30 minutes
  2. concentrationThe resultant mixture was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-13808bc4382147c0974a175fb83b2414
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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