2-Aminothiazole → N-[(6-chloro-3-pyridinyl)methylene]-2-thiazolamine

HRID 628469Notes

Reaction equation

HRID 628469 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](C=O)[N:9]=1.Cl[CH2:17]Cl>>[Cl:7][C:8]1[N:9]=[CH:10][C:11]([CH:17]=[N:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 21552-AminothiazoleHCID 6344DichloromethaneHCID 107968486-Chloro-2-pyridinecarboxaldehyde

Product 1

HCID 86649151N-[(6-chloro-3-pyridinyl)methylene]-2-thiazolamine

Conditions

Temperature
90 °C

Procedure

2-Aminothiazole (0.75 g, 7.5 mmol) was added to 2-chloropyridine-6-carboxaldehyde (1.0 g, 7.1 mmol) in dichloromethane (25 mL) at room temperature. The suspension was stirred an additional 10 min and then concentrated to dryness under vacuum. The resulting residue was heated to 90° C. on a rotary evaporator with a non-returning bump trap to facilitate water removal. After 30 min the resultant yellow solid was checked by NMR to verify reaction completion (by disappearence of the characteristic aldehyde peak at 10.10 ppm (s, 1H)). The title compound was obtained as a yellow solid (1.55 g) and used in the next step without further purification.

Workup

  1. concentrationconcentrated to dryness under vacuum
  2. customwater removal
  3. waitAfter 30 min the resultant yellow solid was checked by NMR
  4. customreaction completion (by disappearence of the characteristic aldehyde peak at 10.10 ppm (s, 1H))

Sources & evidence

ORD record
ord-f77ba3f280fe403d91ecf1e87a180797
Source dataset
uspto-grants-2016_04
Patent number
US09314025B2

Reaction notes

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