(2,4-Dichlorophenoxy)Acetic Acid → HCID 178497368, compound

HRID 1945466Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1.[Cl:13][C:14]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:15]=1[O:16][CH2:17][C:18](O)=O.ClCCl.[OH-].[Na+]>C[Si](OP(=O)=O)(C)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[NH:10][C:18]([CH2:17][O:16][C:15]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:14]=3[Cl:13])=[N:11][C:6]=2[CH:5]=1)=[O:12]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 3,4-diamino-benzoic acid methyl ester (105.24 mg, 0.63 mmol) and 2,4-dichlorophenoxy acetic acid (100 mg, 0.45 mmol) in PPSE (1.5 mL) was heated at 160° C. for 4 h. At the end of the reaction period, the mixture was taken to 3 mL dichloromethane and neutralized with 4.5 mL 1 N NaOH solution. The organic layer was separated and the aqueous solution extracted with 3×3 mL portions of dichloromethane. The combined extracts were dried over anhydrous MgSO4, filtered and the solvent was removed with rotary evaporator under reduced pressure. The residue was purified by flash chromatography (EtOAc:Hexanes=1:1) to afford 2-(2,4-dichloro-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester as a colorless powder (0.121 g, 52% yield).

Workup

customAt the end of the reaction period
customThe organic layer was separated
extractionthe aqueous solution extracted with 3×3 mL portions of dichloromethane
dry with materialThe combined extracts were dried over anhydrous MgSO4
filtrationfiltered
customthe solvent was removed with rotary evaporator under reduced pressure
customThe residue was purified by flash chromatography (EtOAc:Hexanes=1:1)

Sources & evidence

ORD record: ord-fbe37773c0014aaebf3be07607f612fb
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394799B2

Reaction notes

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