Nicotinic Acid → HCID 20257006, compound

HRID 637478Notes

Reaction equation

HRID 637478 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:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32]2[CH:40]=[CH:39][C:35]([CH2:36][CH2:37]O)=[CH:34][CH:33]=2)=[CH:23][CH:22]=1.O>N1C=CC=CC=1>[C:11]([O:19][CH2:37][CH2:36][C:35]1[CH:34]=[CH:33][C:32]([O:31][CH2:30][CH2:29][CH2:28][CH2:27][C:24]2[CH:25]=[CH:26][C:21]([Cl:20])=[CH:22][CH:23]=2)=[CH:40][CH:39]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[N:14][CH:13]=1

Participants

6

Reactant 4

HCID 938Nicotinic AcidHCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 54289667HCID 54289667, compound

Product 1

HCID 20257006HCID 20257006, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzenesulfonyl chloride (7.66 ml, 0.06 mole) is added with stirrin to a 9.2 g (0.075 mole) of nicotinic acid in 30 ml of pyridine, and then 15.2 g (0.05 mole) of 4-(4-chlorophenylbutoxy)phenethyl alcohol is added to the solution. The mixture is stirred as discribed in Example 1. The reaction mixture is poured into water, and extracted with chloroform, the chloroform layer is washed with potassium carbonate solution and water. The chloroform is removed to give a red-syrup. The red-syrup is purified by chromatography on silica gel using a mixture of benzene and chloroform (1:1) as eluent, to give 11 g (53.6%) of a title compound.

Workup

  1. extractionextracted with chloroform
  2. washthe chloroform layer is washed with potassium carbonate solution and water
  3. customThe chloroform is removed
  4. customto give a red-syrup
  5. customThe red-syrup is purified by chromatography on silica gel using
  6. additiona mixture of benzene and chloroform (1:1) as eluent

Sources & evidence

ORD record
ord-9639e6b5248e47a8840323c455916596
Source dataset
uspto-grants-1985_12
Patent number
US04556715

Reaction notes

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