2-Chloro-1,3-thiazole-5-carbaldehyde → N-[(2-chloro-5-thiazolyl)methylene]-3-phenyl-2-pyridinamine

HRID 1023275Notes

Reaction equation

HRID 1023275 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:14][C:15]1[S:16][C:17]([CH:20]=O)=[CH:18][N:19]=1>ClCCl>[Cl:14][C:15]1[S:16][C:17]([CH:20]=[N:1][C:2]2[C:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:18][N:19]=1

Participants

4

Reactant 2

HCID 14797652-Chloro-1,3-thiazole-5-carbaldehydeHCID 27627953-Phenylpyridin-2-amine2×

Product 1

HCID 66973405N-[(2-chloro-5-thiazolyl)methylene]-3-phenyl-2-pyridinamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

2-Amino-3-phenylpyridine (i.e. the product of Step A, 0.342 g, 2.01 mmol) was added to 2-chloro-1,3-thiazole-5-carbaldehyde (0.296 g, 2.01 mmol) in dichloromethane (10 mL) at room temperature. The suspension was stirred for 10 min and then concentrated to dryness under vacuum. The resulting residue was heated to 90° C. for 20 min on a rotory evaporator with a non-returning bump trap to facilitate water removal. The residual yellow solid was again dissolved in dichloromethane (10 mL) and heated to 90° C. on a rotory evaporator for an additional 20 min. At this time the yellow solid was checked by NMR to verify reaction completion. The title compound was obtained as a yellow solid and used in the next step without further purification.

Workup

  1. concentrationconcentrated to dryness under vacuum
  2. customwater removal
  3. dissolutionThe residual yellow solid was again dissolved in dichloromethane (10 mL)
  4. temperatureheated to 90° C. on a rotory evaporator for an additional 20 min
  5. customreaction completion

Sources & evidence

ORD record
ord-041c232bf38e40fc91e81e2df4faac34
Source dataset
uspto-grants-2014_05
Patent number
US08722690B2

Reaction notes

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