Hexachloroethane → HCID 86687144, compound

HRID 1402302Notes

Reaction equation

HRID 1402302 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10]([C@@H:12]2[CH2:16][C@@H:15]([F:17])[CH2:14][N:13]2[CH3:18])=O)=[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.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([C@@H:12]3[CH2:16][C@@H:15]([F:17])[CH2:14][N:13]3[CH3:18])=[N:9][N:8]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86687143HCID 86687143, compound

Product 1

HCID 86687144HCID 86687144, compoundYield 113.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Intermediate 91b (189 mg, 0.79 mmol), Ph3P (416 mg, 1.59 mmol) and Et3N (0.44 mL, 3.17 mmol) in THF (10 mL) at RT was added hexachloroethane (375 mg, 1.59 mmol) portion wise and the mixture stirred for 4 h. The solution was diluted with water and extracted with DCM. The combined organics were dried and concentrated in vacuo. The residue was purified by FCC, using 0-10% [2M NH3 in MeOH] in DCM, to give the title compound as light yellow powder (214 mg, 63%). LCMS (Method 3): Rt 0.42 min, m/z 239 [MH+].

Workup

  1. extractionextracted with DCM
  2. customThe combined organics were dried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-37b072b4a3984a95a67df2eab66a4fcc
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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