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Tetrabutylammonium Fluoride → N-(4-(benzyloxy)pyridin-3-yl)methanesulfonamide

HRID 2068417
Notes
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Reaction equation

HRID 2068417 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][C:28]=1[N:33](S(C)(=O)=O)[S:34]([CH3:37])(=[O:36])=[O:35])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][C:28]=1[NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67217559N-(4-(benzyloxy)pyridin-3-yl)-N-(methylsulfonyl)methane sulfonamide

Product 1

HCID 59233662N-(4-(benzyloxy)pyridin-3-yl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

Tetrabutylammonium fluoride 1 M in THF (12.2 ml, 42 mmol, 2.5 eq) was added to a solution of N-(4-(benzyloxy)pyridin-3-yl)-N-(methylsulfonyl)methane sulfonamide (6 g, 16.8 mmol, 1 eq) in THF at room temperature. The reaction mixture was refluxed at 60° C. for 10 h. The solution was concentrated completely and diluted with water (5 mL) and was allowed to stir for 15 minutes. The solid precipitated was filtered, washed with water and dried under vacuum yielding the expected product as a pale brown solid. 1HNMR (400 MHz, DMSO-d6): δ 3.35 (s, 3H), 5.27 (s, 2H), 7.21 (d, J=5.64 Hz, 1H), 7.36-7.54 (m, 3H), 7.54 d, J=7.28 Hz, 2H), 8.30 (s, 1H), 8.33 (d, J=5.64 Hz, 1H), 9.34 (s, 1H).

Workup

  1. concentrationThe solution was concentrated completely
  2. additiondiluted with water (5 mL)
  3. customThe solid precipitated
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-0b1150148b9f497cb338c7c9b9454fce
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08293909B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes