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

HRID 1760830
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HRID 1760830 반응식
[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]
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참가 물질

4

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HCID 2337BenzocaineHCID 22596833Butyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-carbamoyl chloride

생성물 1

HCID 22596834Ethyl 4-[3-butyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate수율 54%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
40 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-4cce1dadecbc458eb207fe9d2688e57c
출처 데이터셋
uspto-grants-2005_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06844466B2

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