Benzocaine → HCID 22596839, compound

HRID 1760834Notes

Reaction equation

HRID 1760834 reaction equation
[CH2:1]([NH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:14]([CH3:19])([CH3:18])[CH2:13][CH2:12][C:11]([CH3:21])([CH3:20])[C:10]=2[CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:22](Cl)(Cl)=[O:23].[NH2:26][C:27]1[CH:37]=[CH:36][C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:29][CH:28]=1>C1(C)C=CC=CC=1>[CH2:1]([N:7]([C:8]1[CH:17]=[CH:16][C:15]2[C:14]([CH3:19])([CH3:18])[CH2:13][CH2:12][C:11]([CH3:20])([CH3:21])[C:10]=2[CH:9]=1)[C:22](=[O:23])[NH:26][C:27]1[CH:28]=[CH:29][C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:36][CH:37]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 6371PhosgeneHCID 22596837HCID 22596837, compound

Product 1

HCID 22596839HCID 22596839, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of hexyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (17) (635 mg, 2.21 mmole) in 10 mL toluene was treated with 1.0 mL of a 20% phosgene solution in toluene, stirred at room temperature for nine hours and then concentrated in vacuo. The residue was diluted with 15 mL of pyridine and treated with 730 mg of ethyl p-aminobenzoate (2 eq.). The reaction mixture was heated to 40° C. for 15 hours and concentrated in vacuo to provide a orange oil. The product was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes, dry pack) to provide 296 mg (28%) of ethyl 4-[3-hexyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (19) as a yellow oil.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with 15 mL of pyridine
  3. temperatureThe reaction mixture was heated to 40° C. for 15 hours
  4. concentrationconcentrated in vacuo
  5. customto provide a orange oil
  6. customThe product was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes, dry pack)

Sources & evidence

ORD record
ord-54f599906f754d69991f5ab966ed4f9c
Source dataset
uspto-grants-2005_01
Patent number
US06844466B2

Reaction notes

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