Triethylamine → 6-(5-Phenyl-thiazol-2-ylamino)-pyridine-2-carbaldehyde

HRID 1355438Notes

Reaction equation

HRID 1355438 reaction equation
[C:1]1([C:7]2[S:11][C:10]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][OH:20])[N:14]=3)=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.S(=O)(=O)=O.C(N(CC)CC)C>CS(C)=O.O>[C:1]1([C:7]2[S:11][C:10]([NH:12][C:13]3[N:14]=[C:15]([CH:19]=[O:20])[CH:16]=[CH:17][CH:18]=3)=[N:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 18506891[2-(5-Phenyl-thiazol-2-ylamino)-pyridin-6-yl]-methanol2×

Product 1

HCID 185068596-(5-Phenyl-thiazol-2-ylamino)-pyridine-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

[2-(5-Phenyl-thiazol-2-ylamino)-pyridin-6-yl]-methanol (6-4), 0.60g (2.1 mmol) Sulfur trioxide-pyridine (1.01 g, 6.36 mmol) was dissolved in 10 mL anhydrous DMSO and the resulting solution was stirred for 10 min. Triethylamine (2.45 mL, 17.6 mmol) was added followed by addition of [2-(5-Phenyl-thiazol-2-ylamino)-pyridin-6-yl]-methanol (6-4), (0.60 g, 2.1 mmol). After 30 min the reaction was diluted with water and the resulting precipitate was filtered and washed with water to afford the titled compound.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-fb6962daa37a43d3bc6e054d53e8dbe9
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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