Benzoic Acid → HCID 178511090, compound

HRID 1028217Notes

Reaction equation

HRID 1028217 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[C:12]([OH:20])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN1C=CN=C1.O[C@H:28]1[CH2:33][CH2:32][C@H:31]([CH2:34][C:35]#[N:36])[CH2:30][CH2:29]1>C(#N)C>[C:35]([CH2:34][C@H:31]1[CH2:32][CH2:33][C@H:28]([O:19][C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:29][CH2:30]1)#[N:36]

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 13901-MethylimidazoleHCID 73974-Toluenesulfonyl chlorideHCID 178511089HCID 178511089, compound

Product 1

HCID 178511090HCID 178511090, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of p-toluenesulfonyl chloride (4.71 g), benzoic acid (2.52 g), N-methylimidazole (4.9 mL), and acetonitrile (50 mL), an acetonitrile (50 mL) solution of trans-(4-hydroxy-cyclohexyl)-acetonitrile (2.87 g) obtained in Example (41a) was added at 0° C. The reaction mixture was warmed to room temperature, then stirred overnight, and then concentrated. The residue was diluted with ethyl acetate, then washed with water and saturated brine, and then concentrated. The residue was purified by column chromatography (hexane/ethyl acetate) to obtain the title compound (4.42 g, 88%) as a white solid.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with water and saturated brine
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-22b625db80c4489fa702594969b71b0c
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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