Hydrochloric Acid → HCID 51347779, 화합물

HRID 401010노트

반응식

HRID 401010 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.[CH2:17]([O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([N+:29]([O-:31])=[O:30])[C:27]=1[OH:28])[CH:23]=O)[CH3:18].[NH2:32][C:33]([NH2:35])=[O:34].Cl>CCO.CO.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:23]([C:22]2[CH:25]=[C:26]([N+:29]([O-:31])=[O:30])[C:27]([OH:28])=[C:20]([O:19][CH2:17][CH3:18])[CH:21]=2)[NH:32][C:33](=[O:34])[NH:35][C:9]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 936812-(2-Chlorophenyl)-1-phenylethan-1-one2회HCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehyde

생성물 1

HCID 51347779HCID 51347779, 화합물수율 7%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 2-(2-chlorophenyl)-1-phenylethanone (Intermediate 10) (85 mg, 0.37 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (94 mg, 0.45 mmol), and urea (67 mg, 1.1 mmol) in anhydrous EtOH (20 mL) was added concentrated HCl solution (0.1 mL), and the reaction mixture was refluxed for three days. TLC (EtOAc:MeOH=10:1) showed that about 50% of starting materials were consumed, and the reaction mixture was concentrated. The residue was purified by column chromatography (EtOAc:MeOH=40:1) and preparative HPLC to afford Compound 28 as a yellow solid (12 mg, yield: 7.0%). 1H NMR (CD3OD 400 MHz): δ 7.47 (s, 1H), 7.34-7.40 (m, 1H), 7.20 (s, 5H), 7.10-7.13 (m, 1H), 7.05 (s, 1H), 6.80-6.87 (m, 1H), 6.40-6.45 (m, 1H), 5.45 (s, 1H), 3.95-4.10 (m, 2H), 1.37-1.42 (m, 3H); MS (ESI): m/z 466.2 [M+1]+.

후처리

  1. temperaturethe reaction mixture was refluxed for three days
  2. customwere consumed
  3. concentrationthe reaction mixture was concentrated
  4. customThe residue was purified by column chromatography (EtOAc:MeOH=40:1) and preparative HPLC

출처 및 근거

ORD 기록
ord-4023290732394934a59e0a1fc3826456
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741915B2

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