Nicotinic Acid → HCID 13563049, compound

HRID 637477Notes

Reaction equation

HRID 637477 reaction equation
C1(S(Cl)(=O)=O)C=CC=CC=1.[C:11]([OH:19])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[N:14][CH:13]=1.[Cl:20][C:21]1[CH:37]=[CH:36][C:24]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([CH:33](O)[CH3:34])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1.C(Cl)(Cl)Cl>N1C=CC=CC=1>[C:11]([O:19][CH2:34][CH2:33][C:30]1[CH:29]=[CH:28][C:27]([O:26][CH2:25][C:24]2[CH:23]=[CH:22][C:21]([Cl:20])=[CH:37][CH:36]=2)=[CH:32][CH:31]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[N:14][CH:13]=1

Participants

6

Reactant 4

HCID 938Nicotinic AcidHCID 6212ChloroformHCID 7369Benzenesulfonyl chlorideHCID 20257001HCID 20257001, compound

Product 1

HCID 13563049HCID 13563049, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzenesulfonyl chloride (10.6 g, 0.06 mole) is dropped with stirring at 60° C. to a nicotinic acid in 30 ml of pyridine to yield uniform solution. After the solution was stirred at 50°-60° C. for ten minutes, 4-(4-chlorobenzyloxy)phenyl ethanol (13.1 g, 0.05 mole) is added to the solution, and the mixture is stirred for 45 minutes at room temperature. The reaction mixture is poured into 300 ml of ice water to give crystals. The crystals are dissolved into 300 ml of chloroform, the chlorofrom layer is washed with 5% pottassium carbonate solution and water. The chloroform layer is dried over sodium sulfate, and the chloroform is evaporated to give crude crystals. The crude crystals are recrystallized from isopropanol to obtain 15.5 g (84.3%) of a title compound.

Workup

  1. customto yield uniform solution
  2. stirringthe mixture is stirred for 45 minutes at room temperature
  3. customto give crystals
  4. washthe chlorofrom layer is washed with 5% pottassium carbonate solution and water
  5. dry with materialThe chloroform layer is dried over sodium sulfate
  6. customthe chloroform is evaporated
  7. customto give crude crystals
  8. customThe crude crystals are recrystallized from isopropanol

Sources & evidence

ORD record
ord-08e7cbfbce284db0bdd2b1cfa79b88aa
Source dataset
uspto-grants-1985_12
Patent number
US04556715

Reaction notes

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