Hexachloroethane → HCID 178523579, compound

HRID 470712Notes

Reaction equation

HRID 470712 reaction equation
ClC(Cl)(Cl)C(Cl)(Cl)Cl.C(N(CC)CC)C.[CH2:16]([O:23][CH2:24][C:25]([NH:27][NH:28][C:29]([C@H:31]1[CH2:36][CH2:35][C@H:34]([NH:37][C:38](=[O:47])[O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:33][CH2:32]1)=[O:30])=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:16]([O:23][CH2:24][C:25]1[O:30][C:29]([C@H:31]2[CH2:36][CH2:35][C@H:34]([NH:37][C:38](=[O:47])[O:39][CH2:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH2:33][CH2:32]2)=[N:28][N:27]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 178521423HCID 178521423, compound

Product 1

HCID 178523579HCID 178523579, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Hexachloroethane (205 mg, 0.87 mmol), triethylamine (0.29 ml, 2.08 mmol), and the compound (152 mg, 0.35 mmol) obtained in Step 1 above were added to a dichloromethane (9 ml) solution of triphenylphosphine (273 mg, 1.04 mmol) under ice cooling and the resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was diluted with dichloromethane:methanol [10:1 (v/v)], washed with 10% aqueous citric acid solution, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=2:1→1:1 (v/v)] to give 125 mg (86%) of the title compound as a colorless solid.

Workup

  1. washmethanol [10:1 (v/v)], washed with 10% aqueous citric acid solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=2:1→1:1 (v/v)]

Sources & evidence

ORD record
ord-0e1a8ec0f6d241b68844b2ee659614d5
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

Loading…