Hexachloroethane → HCID 69641013, compound

HRID 1502585Notes

Reaction equation

HRID 1502585 reaction equation
[CH2:1]([N:3]([N:11]1[CH:15]=[C:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:13]=[CH:12]1)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:2].[Li+].CCC[CH2-].[Cl:27]C(Cl)(Cl)C(Cl)(Cl)Cl>O1CCCC1>[Cl:27][C:12]1[N:11]([N:3]([CH2:1][CH3:2])[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:7])[CH3:8])[CH:15]=[C:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:13]=1

Participants

5

Reactant 3

HCID 6214HexachloroethaneHCID 61028n-Butyl lithiumHCID 67499538HCID 67499538, compound

Product 1

HCID 69641013HCID 69641013, compoundYield 3.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A vacuum dried 25 mL round bottomed flask equipped with a magnetic stir bar and containing tert-butyl ethyl(4-(pyridin-3-yl)-1H-imidazol-1-yl)carbamate (77 mg, 0.267 mmol) was charged with anhydrous tetrahydrofuran (THF, 3 mL) and cooled to −78° C. N-butyllithium (0.25 mL 0.675 mmol, 2.5 M in hexanes) was added and the mixture was stirred for 15 minutes. Hexachloroethane (189 mg, 0.80 mmol) dissolved in anhydrous THF (1 mL) was added dropwise to the reaction mixture while maintaining a temperature of −78° C. After stirring for 1 hour, the reaction was allowed to warm to room temperature. The reaction mixture was loaded directly on a silica gel column and the THF was removed in a vacuum oven. The crude product was purified using silica gel chromatography (0-25% methanol/dichloromethane) to afford the title compound (3 mg, 0.009 mmol, 3.5%) as a yellow oil: 1H NMR (600 MHz, CDCl3) δ 8.92 (d, J=1.6 Hz, 1H), 8.50 (dd, J=4.8, 1.5 Hz, 1H), 8.06 (dt, J=7.9, 2.0 Hz, 1H), 7.33-7.27 (m, 2H), 3.89 (dq, J=14.5, 7.3 Hz, 1H), 3.68 (dq, J=14.3, 7.2 Hz, 1H), 1.44 (s, 9H), 1.22 (t, J=7.2 Hz, 3H); 13C NMR (151 MHz, CDCl3) δ 152.90, 148.47, 146.02, 136.07, 134.08, 131.81, 128.79, 123.36, 117.66, 83.23, 45.32, 28.04, 13.03; ESIMS m/z 323 ([M+H]+).

Workup

  1. customA vacuum dried 25 mL round bottomed flask
  2. customequipped with a magnetic stir bar
  3. additionwas added dropwise to the reaction mixture
  4. temperaturewhile maintaining a temperature of −78° C
  5. stirringAfter stirring for 1 hour
  6. temperatureto warm to room temperature
  7. customthe THF was removed in a vacuum oven
  8. customThe crude product was purified

Sources & evidence

ORD record
ord-589d2640fe934f149676c0aec036b207
Source dataset
uspto-grants-2015_12
Patent number
US09210931B2

Reaction notes

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