Diisopropylamine → 6-Phenyl-1,2-thiazinane 1,1-dioxide

HRID 517292Notes

Reaction equation

HRID 517292 reaction equation
Br[CH2:2][CH2:3][CH2:4][NH:5][S:6]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])=[O:7].C(NC(C)C)(C)C.[Li]CCCC.[NH4+].[Cl-]>O1CCCC1.CCOC(C)=O.CCOC(C)=O.CCCCCCC.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[C:10]1([CH:9]2[S:6](=[O:8])(=[O:7])[NH:5][CH2:4][CH2:3][CH2:2]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

9

Reactant 4

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 43133750N-(3-bromopropyl)(phenyl)methanesulfonamideHCID 178418339Butyllithium

Product 1

HCID 713039976-Phenyl-1,2-thiazinane 1,1-dioxideYield 80%

Reagents, catalysts & solvents 4

HCID 13181,10-PhenanthrolineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

To a solution of N-(3-bromopropyl)-1-phenylmethanesulfonamide (2.3 g, 7.9 mmol), diisopropylamine (0.28 mL, 2.0 mmol) and 1,10-phenanthroline (3.6 mg, 0.02 mmol) in tetrahydrofuran (26 mL) at −78° C. was added n-BuLi (6.8 mL, 2.5 M in hexanes) dropwise and the reaction was stirred for 16 hours. Saturated NH4Cl was then added and the reaction was diluted with EtOAc, washed with water and brine, dried with MgSO4, concentrated and purified by silica gel column chromatography (0-50% EtOAc/heptane) to 6-Phenyl-1,2-thiazinane 1,1-dioxide (1.3 g, 80% yield). 1H NMR (300 MHz, DMSO-d6) δ 7.40-7.35 (m, 5H), 6.98 (m, 1H), 4.12 (dd, 1H), 3.26-3.20 (m, 2H), 2.40-2.30 (m, 1H), 2.16-2.12 (m, 1H), 1.77-1.65 (m, 2H). LCMS (ESI), m/z, 234 [M+Na]+. (Reference: D. Askin, et al. Org. Lett. 2003, 4175.)

Workup

  1. washwashed with water and brine
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e54cae8a5fa0439e83be5cdac2f7385e
Source dataset
uspto-grants-2015_08
Patent number
US09115101B2

Reaction notes

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