Acetic Acid → HCID 178496989、化合物

HRID 1898349ノート

反応式

HRID 1898349 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.C(O)(=O)C>C1C=CC=CC=1.[Fe]>[NH2:24][C:15]1[C:13]2[NH:14][C:10]([NH:9][C:3]3[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[N:11][C:12]=2[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[C:16]=1[OH:23]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 178496990HCID 178496990、化合物

生成物 1

HCID 178496989HCID 178496989、化合物収率 95.2%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 241Benzene溶媒

実験手順

To a solution of methyl 2-[(2,6-dichlorophenyl)amino]-6-hydroxy-7-nitro-1H-benzimidazole-5-carboxylate (Step-3 of Intermediate-55, 0.500 g) in benzene (2.0 mL) were added iron powder (0.500 g) and acetic acid (2.0 mL). The reaction mass was refluxed for 3 h. Decant the reaction mass removed the solvent under vacuum. The obtained solid mass was washed with water. The reaction mass was extracted with MeOH:DCM (5%). The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 0.440 g of the desired product. 1HNMR (DMSO-d6): δ 3.87 (s, 3H), 4.45 (s, 2H), 7.28-7.47 (m, 1H), 7.53-7.59 (m, 3H), 11.00 (s, 2H).

後処理

  1. temperatureThe reaction mass was refluxed for 3 h
  2. customDecant the reaction mass
  3. customremoved the solvent under vacuum
  4. washThe obtained solid mass was washed with water
  5. extractionThe reaction mass was extracted with MeOH
  6. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-a74f317fc0c64c2fad1e1851936f9b56
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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