Hexachloroethane → HCID 86686954, compound

HRID 2282367Notes

Reaction equation

HRID 2282367 reaction equation
ClC(Cl)(Cl)C(Cl)(Cl)Cl.[C:9]([O:13][C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]([NH:23][NH:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][N:26]=1)=O)=[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[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]1[N:26]2[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:25]2=[N:24][N:23]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86686955HCID 86686955, compound

Product 1

HCID 86686954HCID 86686954, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hexachloroethane (1.34 g, 5.65 mmol) was added portionwise to a solution of Intermediate 6a (917 mg, 2.83 mmol), triphenylphosphine (1.48 g, 5.65 mmol) and triethylamine (1.6 mL, 11.3 mmol) in dry THF (15 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 the title compound as a buff-coloured foam (669 mg, 77%). LCMS (Method 4): Rt 2.48 min, m/z 307 [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-2342379a872f49398a42969a56344906
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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