Hexachloroethane → HCID 66760259, compound

HRID 389421Notes

Reaction equation

HRID 389421 reaction equation
[O:1]1[C:5]2=[C:6]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[Li+].CC([N-]C(C)C)C.[Cl:33][C:34](Cl)(Cl)[C:35]([Cl:38])(Cl)Cl>C1COCC1>[Cl:33][C:2]1[O:1][C:5]2=[C:6]([N:10]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1.[Cl:33][C:34]1[O:1][C:5]2=[C:6]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:7]=[CH:8][CH:9]=[C:4]2[C:35]=1[Cl:38]

Participants

6

Reactant 3

HCID 6214HexachloroethaneHCID 2724682Lithium diisopropylamideHCID 66759326Di-tert-butyl furo[2,3-c]pyridin-7-ylimidodicarbonate

Product 2

HCID 66760259HCID 66760259, compoundYield 65%HCID 66760307Di-tert-butyl (2,3-dichlorofuro[2,3-c]pyridin-7-yl)imidodicarbonateYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Di-tert-butyl furo[2,3-c]pyridin-7-ylimidodicarbonate (25 g, 75.3 mmol) in dry THF (350 mL) was cooled to between −65° C. and −75° C. and LDA (1.8 M in THF/heptanes/ethylbenzene, 50 mL, 90 mmol) was added via syringe over a period of 10 min. The mixture was stirred for 1.5 h between −65° C. and −75° C. and then treated with hexachloroethane (71.2 g, 0.30 mol) in dry THF (150 mL) added via syringe over a 30 min period. The mixture was allowed to warm to RT over 16 h and was quenched by the addition of water (100 mL) and stirred for 10 min. The reaction was diluted with EtOAc, the phases were separated and the aqueous phase was extracted with EtOAc (2×100 mL). The combined organic extracts were washed with water, dried over Na2SO4, filtered and concentrated in vacuo. The crude product thus obtained was purified by flash chromatography using triethylamine coated silica gel eluting (EtOAc:hexane mixtures) to provide 18 g (65%) of di-tert-butyl (2-chlorofuro[2,3-c]pyridin-7-yl)imidodicarbonate and 5 g (18%) of di-tert-butyl (2,3-dichlorofuro[2,3-c]pyridin-7-yl)imidodicarbonate.

Workup

  1. additionadded via syringe over a 30 min period
  2. customwas quenched by the addition of water (100 mL)
  3. stirringstirred for 10 min
  4. additionThe reaction was diluted with EtOAc
  5. customthe phases were separated
  6. extractionthe aqueous phase was extracted with EtOAc (2×100 mL)
  7. washThe combined organic extracts were washed with water
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude product thus obtained
  12. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-6ca167658ae443b7a3cac51ac43f49a4
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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