Benzocaine → HCID 22600032, compound

HRID 1759774Notes

Reaction equation

HRID 1759774 reaction equation
[CH2:1]([NH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]=2[CH:11]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:24](Cl)(Cl)=[O:25].[NH2:28][C:29]1[CH:39]=[CH:38][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][CH:30]=1>C1(C)C=CC=CC=1>[CH2:1]([N:9]([C:10]1[CH:19]=[CH:18][C:17]2[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]=2[CH:11]=1)[C:24](=[O:25])[NH:28][C:29]1[CH:30]=[CH:31][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:38][CH:39]=1)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 6371PhosgeneHCID 22600035HCID 22600035, compound

Product 1

HCID 22600032HCID 22600032, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of phenethyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (9) (619 mg, 2.01 mmole) in 10 mL toluene was treated with 1.5 mL of a 20% phosgene solution in toluene and stirred at room temperature for 12 hours. The reaction mixture was concentrated in vacuo, the residue diluted with 15 mL of pyridine and then treated with 665 mg of ethyl p-aminobenzoate (2 eq.). The mixture was heated at 40° C. for 15 hours, then concentrated in vacuo to provide an orange oil. The product was purified by flash chromatography (SiO2, 15% ethyl acetate/hexanes, dry pack) to yield 441 mg (44%) of ethyl 4-[3-phenethyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (11) as a pale yellow foam.

Workup

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

Sources & evidence

ORD record
ord-b81f1489988e4a118c8e5450dbc1f722
Source dataset
uspto-grants-2005_01
Patent number
US06838472B2

Reaction notes

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