Sodium hydride → 2-Isopropoxy-5-(3-methylpiperidinosulfonyl)benzoic Acid

HRID 1703703Notes

Reaction equation

HRID 1703703 reaction equation
FC1C=CC(S(Cl)(=O)=O)=CC=1C(O)=[O:5].[CH3:15][CH:16]1[CH2:21]CCNC1.F[C:23]1[CH:31]=[CH:30][C:29]([S:32]([N:35]2[CH2:40][CH2:39][CH2:38][CH:37]([CH3:41])[CH2:36]2)(=[O:34])=[O:33])=[CH:28][C:24]=1[C:25]([OH:27])=[O:26].[H-].[Na+]>C(O)(C)C>[CH:16]([O:5][C:23]1[CH:31]=[CH:30][C:29]([S:32]([N:35]2[CH2:40][CH2:39][CH2:38][CH:37]([CH3:41])[CH2:36]2)(=[O:34])=[O:33])=[CH:28][C:24]=1[C:25]([OH:27])=[O:26])([CH3:21])[CH3:15]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 790813-MethylpiperidineHCID 6089842-Fluoro-5-chlorosulfonylbenzoic acidHCID 36511162-Fluoro-5-(3-methylpiperidinosulfonyl)benzoic acid

Product 1

HCID 205059782-Isopropoxy-5-(3-methylpiperidinosulfonyl)benzoic Acid

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Fluoro-5-chlorosulfonylbenzoic acid is reacted with 3-methylpiperidine by the method of Example 1, and the resulting 2-fluoro-5-(3-methylpiperidinosulfonyl)benzoic acid (5 millimoles) is heated on a steam bath for 31/2 hours in isopropyl alcohol (50 ml.) with 5 millimoles of sodium hydride (56.6% suspension in mineral oil). The reaction mixture is evaporated to dryness, and then dissolved in 50 ml. of water. After washing with ether, the aqueous solution is acidified with concentrated HCl. The acid solution is then extracted with ether, and the ether extract washed with water and evaporated to an oil. The oil crystallizes from isopropyl ether-hexane. Recrystallization from the same solvent mixture affords the product, m.p. 102°-104° C.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. dissolutiondissolved in 50 ml
  3. washAfter washing with ether
  4. extractionThe acid solution is then extracted with ether
  5. extractionthe ether extract
  6. washwashed with water
  7. customevaporated to an oil
  8. customThe oil crystallizes from isopropyl ether-hexane
  9. customRecrystallization from the same solvent mixture
  10. customaffords the product, m.p. 102°-104° C.

Sources & evidence

ORD record
ord-d6ab4d0ce68f469491eceaf8f60e962f
Source dataset
uspto-grants-1978_11
Patent number
US04124590

Reaction notes

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