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

HRID 1355498Notes

Reaction equation

HRID 1355498 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), 0.60 g (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-f00b4bac07a74dd19ef5663375215d13
Source dataset
uspto-grants-2003_07
Patent number
US06586424B2

Reaction notes

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