Acetic Acid → HCID 178496987, compound

HRID 1898343Notes

Reaction equation

HRID 1898343 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

HCID 178496987HCID 178496987, compoundYield 51.8%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bd43159d89d74f87a4fd63d13a5cdf5a
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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