Ammonium Chloride → 4-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol

HRID 1405743Notes

Reaction equation

HRID 1405743 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[C:38]3=[N:39][S:40](=[O:44])(=[O:43])[CH2:41][CH2:42][N:37]3[CH:36]=[CH:35][CH:34]=2)=[CH:29][CH:28]=1)(C(C)(C)C)(C)C.[NH4+].[Cl-]>C1COCC1>[O:44]=[S:40]1(=[O:43])[CH2:41][CH2:42][N:37]2[CH:36]=[CH:35][CH:34]=[C:33]([C:30]3[CH:31]=[CH:32][C:27]([OH:26])=[CH:28][CH:29]=3)[C:38]2=[N:39]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 667477259-(4-((Tert-butyl(dimethyl)silyl)oxy)phenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

Product 1

HCID 667478174-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenolYield 96.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1 M in THF) (40.0 mL) was added to a solution of 9-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (14.9 g) in THF (dry)(2.0 L) at 0° C. and the mixture was stirred at ambient temperature for 30 min. The mixture was neutralized with sat. NH4Cl aq. and extracted with EtOAc. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was washed with EtOAc/hexane to give the title compound (10.2 g) as an off-white crystal.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. washThe residue was washed with EtOAc/hexane

Sources & evidence

ORD record
ord-834bd49bef534dcdabed9fbffd8aa057
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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