Benzocaine → HCID 69316798, compound

HRID 2389489Notes

Reaction equation

HRID 2389489 reaction equation
S(Cl)(Cl)=O.[CH:5]1([CH:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([OH:14])=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH2:21]([O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)[CH3:22].C(N(CC)CC)C>CN(C=O)C.ClCCl>[CH2:21]([O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:12](=[O:14])[CH:11]([CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:27][CH:26]=1)[CH3:22]

Participants

7

Reactant 4

HCID 2337BenzocaineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 97942alpha-Cyclohexylphenylacetic acid

Product 1

HCID 69316798HCID 69316798, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a flask containing thionyl chloride (1.52 g, 929 μl, 12.8 mmol) and 1 drop of DMF is added cyclohexylphenylacetic acid (1.87 g, 8.54 mmol). The resulting solution is stirred for 1 h. The thionyl chloride is evaporated under reduced pressure and the resulting crude acid chloride is diluted in dichloromethane (15 ml). To this solution is added dropwise a solution of 4-amino-benzoic acid ethyl ester (1.41 g, 8.54 mmol) and triethylamine (1.49 ml, 1.08 g, 10.67 mmol) in dichloromethane (15 ml). The resulting mixture is stirred for 30 min at rt. It is diluted with dichloromethane and the resulting organic phase is washed with a 10% aqueous citric acid solution, with a saturated aqueous Na2CO3 solution and with water. It is dried over Na2SO4 and the solvent is evaporated in vacuo. The crude residue is purified on silica gel (AcOEt/heptane, 1.4), yielding the title compound (3.04 g) in 97% as a white solid: tR=8.00 min (LC-1), ESI-MS (pos.): m/z 366.18 [M+H]+, ESI-MS (neg.): m/z 364.25 [M−H]+.

Workup

  1. customThe thionyl chloride is evaporated under reduced pressure
  2. additionthe resulting crude acid chloride is diluted in dichloromethane (15 ml)
  3. stirringThe resulting mixture is stirred for 30 min at rt
  4. washthe resulting organic phase is washed with a 10% aqueous citric acid solution, with a saturated aqueous Na2CO3 solution and with water
  5. dry with materialIt is dried over Na2SO4
  6. customthe solvent is evaporated in vacuo
  7. customThe crude residue is purified on silica gel (AcOEt/heptane, 1.4)

Sources & evidence

ORD record
ord-9ca80f3b5e894d6c8f3e14bea5af6040
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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