Trichloroacetyl chloride → HCID 90191807, compound

HRID 2201658Notes

Reaction equation

HRID 2201658 reaction equation
[CH2:1]=[C:2]1[CH2:5][CH:4]([CH2:6][NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.[C:18]([C:22](Cl)=[O:23])(Cl)([Cl:20])[Cl:19].C(=O)(O)[O-].[Na+]>C(OCC)C.CC(N(C)C)=O.[Cu].[Zn]>[Cl:19][C:18]1([Cl:20])[C:22](=[O:23])[CH2:1][C:2]21[CH2:3][CH:4]([CH2:6][NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5]2

Participants

7

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 86723563HCID 86723563, compound

Product 1

HCID 90191807HCID 90191807, compound

Reagents, catalysts & solvents 3

HCID 10290809Zinc copper coupleCatalystHCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Procedure

Compound 4-3 (3 g, 12.98 mmol) and zinc-copper alloy (7.78 g, 64.9 mmol) were placed in 100 mL of diethyl ether, added dropwise a solution of CCl3COCl (6.97 g, 38.33 mmol) dissolved in 15 mL of DMA with stirring slowly. After the completion of addition, the mixture was stirred at room temperature for 18 hours. To the reaction mixture was poured 100 mL of saturated aqueous solution of sodium bicarbonate, and suction filtrated to remove insolubles, liquid separated, the aqueous phase was extracted with diethyl ether. The organic phases were combined, dried over anhydrous sodium sulfate, suction filtrated to remove the desiccant, and rotary evaporated to remove solvents, the resulting crude Compound 4-4 was used directly in the next reaction.

Workup

  1. additionAfter the completion of addition
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. filtrationfiltrated
  4. customto remove insolubles, liquid
  5. customseparated
  6. extractionthe aqueous phase was extracted with diethyl ether
  7. dry with materialdried over anhydrous sodium sulfate, suction
  8. filtrationfiltrated
  9. customto remove the desiccant, and
  10. customrotary evaporated
  11. customto remove solvents
  12. customthe resulting crude Compound 4-4 was used directly in the next reaction

Sources & evidence

ORD record
ord-015a2953c78f494286fb629857878c1c
Source dataset
uspto-grants-2016_06
Patent number
US09365499B2

Reaction notes

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