Hexachloroethane → HCID 86731254, compound

HRID 2277195Notes

Reaction equation

HRID 2277195 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:23]=[CH:22][C:9]([C:10]([NH:12][C:13]3[C:18]([OH:19])=[CH:17][C:16]([OH:20])=[CH:15][C:14]=3[F:21])=O)=[CH:8][C:7]=2[F:24])[CH2:3][CH2:2]1.ClC(Cl)(Cl)C(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C(#N)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:23]=[CH:22][C:9]([C:10]3[O:19][C:18]4[CH:17]=[C:16]([OH:20])[CH:15]=[C:14]([F:21])[C:13]=4[N:12]=3)=[CH:8][C:7]=2[F:24])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86731255HCID 86731255, compound

Product 1

HCID 86731254HCID 86731254, compoundYield 5.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(cyclopropylmethoxy)-3-fluoro-N-(2-fluoro-4,6-dihydroxyphenyl)benzamide (2.29 g), hexachloroethane (4.04 g) and triphenylphosphine (4.48 g) in acetonitrile (50 mL) was added triethylamine (2.86 mL) at 0° C., and the mixture was stirred at room temperature for 15 min, and then with heating at 80° C. for 1 hr. The reaction mixture was filtered, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (110 mg). 1H NMR (300 MHz, CDCl3) δ 0.37-0.45 (2H, m), 0.65-0.74 (2H, m), 1.24-1.44 (1H, m), 3.97 (2H, d, J=7.2 Hz), 5.26 (1H, d, J=3.4 Hz), 6.97-7.10 (2H, m), 7.38 (1H, dd, J=8.5, 1.3 Hz), 7.87-7.98 (2H, m).

Workup

  1. temperaturewith heating at 80° C. for 1 hr
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bc2a7013cca94f4883d72de914c87174
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

Loading…