Hexachloroethane → HCID 86687163, compound

HRID 2285157Notes

Reaction equation

HRID 2285157 reaction equation
ClC(Cl)(Cl)C(Cl)(Cl)Cl.[F:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][NH:17][C:18]([N:20]([CH2:24][CH:25]=[CH2:26])[CH2:21][CH:22]=[CH2:23])=O)=[N:14][CH:15]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CO>[CH2:21]([N:20]([CH2:24][CH:25]=[CH2:26])[C:18]1[N:14]2[CH:15]=[C:10]([F:9])[CH:11]=[CH:12][C:13]2=[N:16][N:17]=1)[CH:22]=[CH2:23]

Participants

7

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86687162HCID 86687162, compound

Product 1

HCID 86687163HCID 86687163, compoundYield 62.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Hexachloroethane (4.34 g, 18.4 mmol) was added portionwise over 5 min at RT to a stirred mixture of Intermediate 101a (2.30 g, 9.2 mmol), triethylamine (3.71 g, 36.8 mmol) and triphenylphosphine (4.82 g, 18.4 mmol) in THF (90 mL). The reaction mixture was stirred at RT for 1 h, then diluted with MeOH and purified by FCC using SCX-2 cartridge. The cartridge was washed with MeOH and the product was eluted with 2M NH3 in MeOH. The compound containing fractions were combined and concentrated in vacuo. The resultant residue was subjected to the follow purification procedure; FCC on silica (0-6% [2M NH3 in MeOH] in DCM), then SCX-2 cartridge (conditions described above) and finally further FCC on silica (0-2% MeOH in EtOAc), to afford the title compound (1.34 g, 62%). 1H NMR (400 MHz, CDCl3): 3.87 (4H, d, J=6.2 Hz), 5.16-5.35 (4H, m), 5.85-6.02 (2H, m), 7.11 (1H, ddd, J=10.0, 7.6, 2.3 Hz), 7.58-7.67 (1H, m), 7.75-7.80 (1H, m).

Workup

  1. custompurified by FCC
  2. washThe cartridge was washed with MeOH
  3. washthe product was eluted with 2M NH3 in MeOH
  4. additionThe compound containing fractions
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was subjected to the follow purification procedure

Sources & evidence

ORD record
ord-478183af6032416dbdd52936c154afb7
Source dataset
uspto-grants-2015_09
Patent number
US09145413B2

Reaction notes

Loading…