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

HRID 1474065Notes

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 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

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

Sources & evidence

ORD record: ord-e0380ddb1567430cbff8c2b2ad4328b6
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018220B2

Reaction notes

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