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Pyridine → HCID 22346411, compound

HRID 897331
Notes
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Reaction equation

HRID 897331 reaction equation
C([O:9][C:10]1[C:19]2[N:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13](=[O:20])[NH:12][C:11]=1[C:21]([O:23][CH3:24])=[O:22])(=O)C1C=CC=CC=1.N1C=CC=CC=1.[O:31](S(C(F)(F)F)(=O)=O)[S:32]([C:35]([F:38])([F:37])[F:36])(=O)=[O:33]>ClCCl>[OH:9][C:10]1[C:11]([C:21]([O:23][CH3:24])=[O:22])=[N:12][C:13]([O:20][S:32]([C:35]([F:38])([F:37])[F:36])(=[O:33])=[O:31])=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 22346242HCID 22346242, compound

Product 1

HCID 22346411HCID 22346411, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring suspension of the compound of Step 2 (25 g, 77 mmol) in dry dichoromethane (150 ml) under argon was added pyridine (31 ml, 385 mmol). The suspension was then cooled to 0° C. and Tf2O (32.6 g, 19.4 ml, 116 mmol) was added dropwise which caused the formation of a red color. The ice bath was then removed and after 1 hour the red solution was poured into a saturated aqueous solution of NaHCO3 (200 ml). The organic phase was separated and the aqueous phase was extracted three times with chloroform. The combined organics were dried over sodium sulfate, filtered and concentrated to give a green solid.

Workup

  1. customThe ice bath was then removed and after 1 hour the red solution
  2. additionwas poured into a saturated aqueous solution of NaHCO3 (200 ml)
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted three times with chloroform
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a green solid

Sources & evidence

ORD record
ord-497d3110222e43a7aceb44e404f68e8a
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06921759B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes