Hexachloroethane → HCID 46869072, compound

HRID 2098160Notes

Reaction equation

HRID 2098160 reaction equation
[C:1]([NH:4][NH:5][C:6]([C:8]1[S:9][CH:10]=[CH:11][C:12]=1[NH:13][C:14](=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)=[O:7])(=O)[CH3:2].C(N(C(C)C)CC)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C(Cl)(Cl)Cl>C(#N)C>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][C:14]([NH:13][C:12]2[CH:11]=[CH:10][S:9][C:8]=2[C:6]2[O:7][C:1]([CH3:2])=[N:4][N:5]=2)=[O:24])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 68756188HCID 68756188, compound

Product 1

HCID 46869072HCID 46869072, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-(2-(2-acetylhydrazinecarbonyl)thiophen-3-yl)-2-(4-methoxyphenyl)acetamide (300 mg, 0.86 mmol) in anh. acetonitrile (6 mL) was added diisopropylethylamine (0.8 mL, 4.84 mmol) and triphenylphosphine (396 mg, 1.51 mmol). After 5 min, hexachloroethane (292 mg, 1.23 mmol) was added to the reaction mixture and then stirred at room temperature overnight under N2(g) inlet. The reaction mixture was evaporated under reduced pressure, partitioned between ethyl acetate and H2O, dried (sodium sulfate), filtered and concentrated under reduced pressure. Purification by flash column chromatography (silica, 40:60 ethyl acetate/hexane) gave 2-(4-methoxyphenyl)-N-(2-(5-methyl-1,3,4-oxadiazol-2-yl)thiophen-3-yl)acetamide (25 mg, 9%). See James, C. A. et al., Tet. Lett. 47 (2006) 511-514. Method [7] m/z 330.0 (M+H); retention time=4.805. 1H-NMR (CDCl3) δ 10.15 (broad s, 1H), 8.18 (d, J=5.4 Hz, 1H), 7.43 (d, J=5.4 Hz, 1H), 7.31 (d, J=7.6 Hz, 2H), 6.92 (d, J=7.6 Hz, 2H), 3.81 (s, 3H), 3.75 (s, 2H), 2.75 (s, 3H).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. custompartitioned between ethyl acetate and H2O
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography (silica, 40:60 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-339253ffec6e41a3b9ac2cb3c03911a2
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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