3-Pyridinecarbonyl chloride, hydrochloride (1:1) → HCID 88659068, compound

HRID 978414Notes

Reaction equation

HRID 978414 reaction equation
[CH2:1]([O:6][CH2:7][CH:8]([OH:23])/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]2[NH:19][CH:20]=[CH:21][N:22]=2)=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH3:5].Cl.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31](Cl)=[O:32])[CH:26]=1>N1C=CC=CC=1>[CH2:1]([O:6][CH2:7][CH:8]([O:23][C:31]([C:27]1[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=1)=[O:32])/[CH:9]=[CH:10]/[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][C:18]2[NH:19][CH:20]=[CH:21][N:22]=2)=[CH:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 88637290HCID 88637290, compound

Product 1

HCID 88659068HCID 88659068, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

400 mg (1.3 mmol) of E-4-pentyloxy-1-[4-(1-imidazolylmethyl)phenyl]but-1-en-3-ol (5a) were dissolved in 10 ml of dry pyridine, and 409 mg (1.5 mmol) of 3-pyridinecarbonyl chloride hydrochloride were added. The mixture was stirred at room temp. for 8 h, and the solvent was substantially removed in vacuo, and the residue was partitioned between saturated aqueous sodium bicarbonate solution and methylene chloride. The aqueous phase was extracted twice with methylene chloride. Drying of the combined organic phases with magnesium sulfate and removal of the solvent in vacuo produced, after chromatography on silica gel (ethyl acetate/methanol=10:1, Rf=0.20), 380 mg (0.91 mmol, 70%) of ester 6a as a colorless oil.

Workup

  1. customthe solvent was substantially removed in vacuo
  2. customthe residue was partitioned between saturated aqueous sodium bicarbonate solution and methylene chloride
  3. extractionThe aqueous phase was extracted twice with methylene chloride
  4. dry with materialDrying of the combined organic phases with magnesium sulfate and removal of the solvent in vacuo
  5. customproduced

Sources & evidence

ORD record
ord-8a0b58b98ad84c0e9ee5ff47cd78abbb
Source dataset
uspto-grants-1987_05
Patent number
US04665080

Reaction notes

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