Acetic Acid → HCID 178496987、化合物

HRID 1898343ノート

反応式

HRID 1898343 の反応式
[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

参加物

8

反応物 4

HCID 176Acetic AcidHCID 15050Trimethyl orthoacetateHCID 5359967IndiumHCID 178496990HCID 178496990、化合物

生成物 1

HCID 178496987HCID 178496987、化合物収率 51.8%

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bd43159d89d74f87a4fd63d13a5cdf5a
出典データセット
uspto-grants-2013_08
特許番号
US08519149B2

反応ノート

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