Oxalyl chloride → HCID 20571271, compound

HRID 903019Notes

Reaction equation

HRID 903019 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[Cl:7][C:8]1[C:13]([NH:14][S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])=[CH:12][CH:11]=[CH:10][N:9]=1>C(Cl)Cl>[Cl:7][C:8]1[C:13]([N:14]([S:15]([C:18]([F:21])([F:19])[F:20])(=[O:17])=[O:16])[C:2]([C:1]([N:14]([C:13]2[C:8]([Cl:7])=[N:9][CH:10]=[CH:11][CH:12]=2)[S:15]([C:18]([F:19])([F:20])[F:21])(=[O:16])=[O:17])=[O:5])=[O:3])=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 20571255HCID 20571255, compound

Product 1

HCID 20571271HCID 20571271, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Oxalyl chloride (0.762 gram; 0.006 mole) is added dropwise to a suspension of N-(2-chloro-3-pyridyl)trifluoromethanesulfonamide (2.61 grams; 0.01 mole) and powdered molecular sieves (5.0 grams; Molecular Sieve, Type 3A) in methylene chloride (75 mls) at 0° C. under a nitrogen atmosphere. The mixture is then heated to 60° C., held thereat for 3 hours, and then stirred at room temperature for 60 hours. The reaction mixture is filtered and the filtrate is evaporated to dryness. The resulting residue is extracted with diethyl ether, and the combined ethereal extracts are dried over anhydrous sodium sulfate. The dried ethereal extract is then separated and evaporated to obtain 2.33 grams (81% of theoretical) of crude product.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated to dryness
  3. extractionThe resulting residue is extracted with diethyl ether
  4. dry with materialthe combined ethereal extracts are dried over anhydrous sodium sulfate
  5. extractionThe dried ethereal extract
  6. customis then separated
  7. customevaporated
  8. customto obtain 2.33 grams (81% of theoretical) of crude product

Sources & evidence

ORD record
ord-28d3e0ec4e7c4c0baba797cef3c86684
Source dataset
uspto-grants-1980_10
Patent number
US04226738

Reaction notes

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