1,2-Dichloroethane → HCID 89445230, compound

HRID 1771827Notes

Reaction equation

HRID 1771827 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.[CH3:19][O:20][NH:21][CH3:22].C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:7][C:3]=1[C:4]([N:21]([O:20][CH3:19])[CH3:22])=[O:5]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 463123323',4-Difluoro-[1,1'-biphenyl]-3-carboxylic acid

Product 1

HCID 89445230HCID 89445230, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-fluoro-5-(3-fluorophenyl)benzoic acid (intermediate III(a)) (2 g, 8.5 mmol, 1.0 eq) and N-methoxymethanamine hydrochloride (916 mg, 9.4 mmol, 1.1 eq) in DMF (20 mL) was added triethylamine (3.6 mL, 25.6 mmol, 3.0 eq) at 0° C. HOBt (1.51 g, 11.1 mmol, 1.3 eq) and EDC (2.13 g, 11.1 mmol, 1.3 eq) were added and the solution was stirred for 2 days. Water was added and the aqueous layer was extracted with EtOAc. The organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether: EtOAc, 20:1 to 10:1 then CH2Cl2) to give the title compound as a colorless oil (2.03 g, 85%).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe organic extracts were washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue obtained
  7. customwas purified by column chromatography (petroleum ether

Sources & evidence

ORD record
ord-78b1e2a907384e5e897f31aa68edb752
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

Loading…