Hexachloroethane → HCID 86687102, compound

HRID 2285082Notes

Reaction equation

HRID 2285082 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10](=O)[C:11]([CH3:18])([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH3:12])=[N:6][CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC.ClC(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([C:11]([CH3:18])([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH3:12])=[N:9][N:8]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86687101HCID 86687101, compound

Product 1

HCID 86687102HCID 86687102, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 80a (260 mg, 0.98 mmol), Ph3P (511 mg, 1.95 mmol) and Et3N (544 μL, 3.91 mmol) in THF (10.0 mL) at 0° C. was added hexachloroethane (462 mg, 1.95 mmol). The reaction was stirred at RT overnight then partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was taken up in MeOH and loaded onto an SCX-2 cartridge, which was washed with MeOH and eluted with 2M NH3 in MeOH. The reaction showed 50% conversion so was re-submitted to the reaction conditions overnight at 50° C. The workup and purification procedures were repeated to give the title compound (209 mg, 86%). 1H NMR (300 MHz, CDCl3): 1.64 (6H, s), 1.74-1.82 (4H, m), 2.52-2.57 (4H, m), 7.16 (1H, ddd, J 9.8, 7.4, 2.3), 7.69 (1H, m), 8.93 (1H, ddd, J 4.5, 2.3, 0.7).

Workup

  1. customthen partitioned between EtOAc and water
  2. extractionThe aqueous layer was then extracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. washwas washed with MeOH
  8. washeluted with 2M NH3 in MeOH
  9. customso was re-submitted to the reaction conditions overnight at 50° C
  10. customThe workup and purification procedures

Sources & evidence

ORD record
ord-5448f8bea1dd46be9003b05fc463b28e
Source dataset
uspto-grants-2015_09
Patent number
US09145413B2

Reaction notes

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