Sodium → HCID 9908588, compound

HRID 1608954Notes

Reaction equation

HRID 1608954 reaction equation
[Na].[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.Cl[CH2:18][CH2:19][CH2:20][S:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=[O:25]>CC(O)C>[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:18][CH2:19][CH2:20][S:21][C:22]3[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=3[C:24]([OH:26])=[O:25])=[CH:14][CH:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 20083406HCID 20083406, compoundHCID 20083426HCID 20083426, compound

Product 1

HCID 9908588HCID 9908588, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To the solution of 1.3 g (58 mmol) sodium in 100 ml ethanol one adds 5.7 g (29 mmol) 4-[2-(4-pyridinyl)-ethyl]-phenol, stirs for 10 min at room temperature, adds thereto 6.7 g (29 mmol) 2-(3-chloropropylthio)-benzoic acid and heats under reflux for 12 h. One allows to cool, filters, evaporates the filtrate, takes up in water, washes with ether, adjusts the aqueous phase to pH 5 and extracts with dichloromethane. After chromatography of the extract on silica gel and trituration with ligroin, one isolates 2.1 g of title compound (19% of theory) of the m.p. 151°-153° C.

Workup

  1. additionadds
  2. temperatureunder reflux for 12 h
  3. temperatureto cool
  4. customfilters, evaporates the filtrate
  5. extractionAfter chromatography of the extract on silica gel and trituration with ligroin, one

Sources & evidence

ORD record
ord-36cc31b8d99b4f84aaa0bcb2d8293e7a
Source dataset
uspto-grants-1995_03
Patent number
US05399575

Reaction notes

Loading…