Hexachloroethane → HCID 86686960, compound

HRID 630704Notes

Reaction equation

HRID 630704 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]([NH:20][CH:21]([CH3:23])[CH3:22])=O)=[N:14][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C1COCC1>[F:9][C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:18]([NH:20][CH:21]([CH3:23])[CH3:22])=[N:17][N:16]=2)[CH:15]=1

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86686959HCID 86686959, compound

Product 1

HCID 86686960HCID 86686960, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hexachloroethane (1.77 g, 7.75 mmol) was added portionwise to a solution of Intermediate 8a 822 mg, 3.87 mmol), triphenylphosphine (2.03 g, 7.75 mmol) and triethylamine (2.2 mL, 15.49 mmol) in dry THF (15 mL) at RT and stirred for 16 h. The resulting precipitate was filtered off and the filtrate evaporated. The residue was purified by SCX-2, eluting with MeOH followed by 2M NH3 in MeOH, to give the title compound as a buff-coloured foam (618 mg, 82%). LCMS (Method 1): Rt 1.55 min, m/z 195 [MH+].

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. customthe filtrate evaporated
  3. customThe residue was purified by SCX-2
  4. washeluting with MeOH

Sources & evidence

ORD record
ord-fffa532cecae4158926b2669c404aeaf
Source dataset
uspto-grants-2016_04
Patent number
US09315503B2

Reaction notes

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