Pyridinium chloride → HCID 135545348, compound

HRID 1247227Notes

Reaction equation

HRID 1247227 reaction equation
Cl.N1C=CC=CC=1.C[O:9][C:10]1[CH:11]=[C:12]([C:27](O)([CH3:29])[CH3:28])[C:13]2[O:17][C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=3)=[N:15][C:14]=2[CH:26]=1>O>[OH:24][C:21]1[CH:20]=[CH:19][C:18]([C:16]2[O:17][C:13]3[C:12]([C:27]([CH3:29])=[CH2:28])=[CH:11][C:10]([OH:9])=[CH:26][C:14]=3[N:15]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 21907383HCID 21907383, compound

Product 1

HCID 135545348HCID 135545348, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pyridine hydrochloride (400 mg) was heated to 190° C. To the melt was added 2-[5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole-7-yl] propan-2-ol (114 mg, 0.36 mmol) and the reaction was stirred for 2 h. The mixture was cooled to room temperature, dissolved in water and extracted with EtOAc. The organic layers were combined and washed with HCl (1N), water then brine and dried over MgSO4. Evaporation and purification by flash chromatography (50%–60% EtOAc/petroleum ether) gave (40 mg, 41% yield) of the product as a light red-brown solid, m.p. 225–228° C.; MS m/e 268 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with HCl (1N), water
  3. dry with materialbrine and dried over MgSO4
  4. customEvaporation and purification by flash chromatography (50%–60% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-4234cfca03ac4e6d87b86e59eb629aaa
Source dataset
uspto-grants-2006_10
Patent number
US07129258B2

Reaction notes

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