Benzocaine → Ethyl 4-[3-butyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate

HRID 1760830Notes

Reaction equation

[CH2:1]([N:5]([C:9]1[CH:18]=[CH:17][C:16]2[C:15]([CH3:20])([CH3:19])[CH2:14][CH2:13][C:12]([CH3:22])([CH3:21])[C:11]=2[CH:10]=1)[C:6](Cl)=[O:7])[CH2:2][CH2:3][CH3:4].[NH2:23][C:24]1[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=1>N1C=CC=CC=1>[CH2:1]([N:5]([C:9]1[CH:18]=[CH:17][C:16]2[C:15]([CH3:20])([CH3:19])[CH2:14][CH2:13][C:12]([CH3:22])([CH3:21])[C:11]=2[CH:10]=1)[C:6](=[O:7])[NH:23][C:24]1[CH:25]=[CH:26][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:33][CH:34]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of butyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-carbamoyl chloride (9) (368 mg, 0.55 mmole) in 30 mL pyridine was treated with 272 mg of ethyl p-aminobenzoate (3 eq.) and stirred at 40° C. for 15 hours. The reaction mixture was concentrated in vacuo to provide an orange oil which was purified by flash chromatography (SiO2, 2.5% methanol/dichloromethane) which yielded 131 mg (54%) of ethyl 4-[3-butyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (11) as a pale yellow oil.

Workup

concentrationThe reaction mixture was concentrated in vacuo
customto provide an orange oil which
customwas purified by flash chromatography (SiO2, 2.5% methanol/dichloromethane) which

Sources & evidence

ORD record: ord-4cce1dadecbc458eb207fe9d2688e57c
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06844466B2

Reaction notes

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