Hexachloroethane → HCID 86686957, compound

HRID 1402094Notes

Reaction equation

HRID 1402094 reaction equation
ClC(Cl)(Cl)C(Cl)(Cl)Cl.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]([NH:25][NH:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][N:28]=2)=O)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C1COCC1>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[N:28]3[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:27]3=[N:26][N:25]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86686956HCID 86686956, compound

Product 1

HCID 86686957HCID 86686957, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hexachloroethane (893 mg, 3.77 mmol) was added portionwise to a solution of Intermediate 7a (667 mg, 1.89 mmol), triphenylphosphine (990 mg, 3.77 mmol) and triethylamine (1.05 mL, 7.55 mmol) in dry THF (20 mL) at RT and stirred for 4 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 an off-white solid. This was triturated (diethyl ether) to give the title compound as a colourless solid LCMS (Method 1): Rt 2.33 min, m/z 336 [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
  5. customto give an off-white solid
  6. customThis was triturated (diethyl ether)

Sources & evidence

ORD record
ord-aa65062ddc4d4d6db8b60e7ba4870670
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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