1,2-Dichloroethane → 2-(2,4-Dichloro-benzoyl)-6-m-tolyl-benzofuran-3-carboxylic acid amide

HRID 29240Notes

Reaction equation

HRID 29240 reaction equation
[Cl:1][C:2]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:3]=1[C:4]([C:6]1[O:7][C:8]2[CH:17]=[C:16]([C:18]3[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)[CH:15]=[CH:14][C:9]=2[C:10]=1[C:11](O)=[O:12])=[O:5].C(Cl)CCl.C1C=CC2N(O)N=[N:40]C=2C=1.[NH4+].[OH-]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:3]=1[C:4]([C:6]1[O:7][C:8]2[CH:17]=[C:16]([C:18]3[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)[CH:15]=[CH:14][C:9]=2[C:10]=1[C:11]([NH2:40])=[O:12])=[O:5]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 597889522-(2,4-Dichloro-benzoyl)-6-m-tolyl-benzofuran-3-carboxylic acid

Product 1

HCID 597889402-(2,4-Dichloro-benzoyl)-6-m-tolyl-benzofuran-3-carboxylic acid amideYield 78%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2,4-Dichloro-benzoyl)-6-m-tolyl-benzofuran-3-carboxylic acid from step 6 (61.2 mg, 0.14 mmol, 1 eq) in anhydrous THF (3 mL) solution were added EDC (60.0 mg, 0.31 mmol, 2.2 eq) and HOBt (50.0 mg, 0.37 mmol, 2.6 eq). The reaction mixture was stirred at rt for 1 h. A 30% aq. NH4OH solution (0.5 mL) was added to the reaction mixture and stirring was continued for 15 h. The reaction mixture was poured into EtOAc (10 mL). The organic layer were washed with 1N NaOH (5 mL), 1N HCl (5 mL), brine (5 mL). The organic layer was dried over Na2SO4, filtrated, and evaporated in vacuo. The residue was purified by pre-TLC (10% Acetone/DCM) to afford an yellow solid (46.2 mg, 78%) as product. 1H-NMR (CDCl3): δ 9.39 (broad, NH, 1H), 8.58 (d, J=8.3 Hz, 1H), 7.68 (dd, J=1.5, 8.3 Hz, 1H), 7.63 (s, 1H), 7.51 (d, J=1.5 Hz, 1H), 7.48 (d, J=8.3 Hz, 1H), 7.43-7.40 (m, 3H), 7.32 (t, 1H), 7.18 (d, J=8.3 Hz, 1H), 6.01 (broad, NH, 1H), 2.42 (s, 3H); LC-MS (MH+=424/426).

Workup

  1. stirringstirring
  2. waitwas continued for 15 h
  3. washThe organic layer were washed with 1N NaOH (5 mL), 1N HCl (5 mL), brine (5 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltrated
  6. customevaporated in vacuo
  7. customThe residue was purified by pre-TLC (10% Acetone/DCM)

Sources & evidence

ORD record
ord-4afcd3eba0d44ac1a34a466ef380323c
Source dataset
uspto-grants-2008_09
Patent number
US07420066B2

Reaction notes

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