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

HRID 1038869Notes

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][C:11]([CH:14]=O)=[CH:10][N:9]=1>ClCCl>[Cl:7][C:8]1[N:9]=[CH:10][C:11]([CH:14]=[N:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 90 °C

Procedure

2-Aminothiazole (0.75 g, 7.5 mmol) was added to 2-chloropyridine-5-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 rotory 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 disappearance 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

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

Sources & evidence

ORD record: ord-e75284901f9442a58b5e265a8e213c33
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552007B2

Reaction notes

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