Acetic Acid → HCID 178496987, 화합물

HRID 1898343노트

반응식

HRID 1898343 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:14][C:13]2[C:15]([N+:24]([O-])=O)=[C:16]([OH:23])[C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:18][C:12]=2[N:11]=1.[In].[C:28](O)(=O)[CH3:29].C(OC)(OC)(OC)C>C1C=CC=CC=1.C(Cl)Cl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:14][C:13]2[C:15]3[N:24]=[C:28]([CH3:29])[O:23][C:16]=3[C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:18][C:12]=2[N:11]=1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 15050Trimethyl orthoacetateHCID 5359967IndiumHCID 178496990HCID 178496990, 화합물

생성물 1

HCID 178496987HCID 178496987, 화합물수율 51.8%

시약·촉매·용매 3

HCID 241Benzene용매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of methyl 2-[(2,6-dichlorophenyl)amino]-6-hydroxy-7-nitro-1H-benzimidazole-5-carboxylate (0.150 g, 0.370 mmol) in benzene (5 mL), indium (0.172 g, 1.51 mmol), acetic acid (0.468 g, 7.54 mmol) and trimethyl orthoacetate (0.480 g, 2.96 mmol) were added under N2 atmosphere. The reaction mass was refluxed for 3-4 h. A mixture of MeOH:DCM (15%) was added to the reaction mixture. The reaction mass was filtered. The organic layer was concentrated. The obtained product was further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH: DCM to afford 0.075 g of the desired product. 1HNMR (DMSO-d6): δ 2.63 (s, 3H), 3.88 (s, 3H), 7.40 (m, 1H), 7.61-7.69 (m, 3H), 9.56 (s, 1H), 11.56 (s, 1H); MS [M+H]+: 391.33.

후처리

  1. temperatureThe reaction mass was refluxed for 3-4 h
  2. filtrationThe reaction mass was filtered
  3. concentrationThe organic layer was concentrated
  4. customThe obtained product was further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH

출처 및 근거

ORD 기록
ord-bd43159d89d74f87a4fd63d13a5cdf5a
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08519149B2

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