Sodium hydride → 2-(1,1-Dioxo-1lambda6-[1,2]thiazinan-2-yl)-benzonitrile

HRID 1822718Notes

Reaction equation

HRID 1822718 reaction equation
[H-].[Na+].[S:3]1(=[O:10])(=[O:9])[CH2:8][CH2:7][CH2:6][CH2:5][NH:4]1.F[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15]>CN(C=O)C.O>[O:9]=[S:3]1(=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 678552-FluorobenzonitrileHCID 3035081,4-Butanesultam

Product 1

HCID 235683982-(1,1-Dioxo-1lambda6-[1,2]thiazinan-2-yl)-benzonitrileYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (0.54 g, 95%, 20 mmol) in DMF (25 mL) was added [1,2]thiazinane 1,1-dioxide (2.70 g, 20 mmol). After stirring the mixture at room temperature for 15 min, 2-fluorobenzonitrile (2.7 mL, 25 mmol) was added and the resulting mixture was stirred at 80° C. for 18 h, cooled, diluted with water and the resulting solid filtered. The mother liquor was concentrated and the residue was recrystalized from 1:1 ethyl acetate/hexanes to yield the title product as an orange solid (3.47 g, 74% yield). 1HNMR (500 MHz, CDCl3) δ: 7.69 (1H, dd, J=7.63, 1.23 Hz), 7.62–7.55 (2H, m) 7.40 (1H, t, J=7.63 Hz), 3.72 (2H, t, J=5.19 Hz), 3.31 (2H, t, J=6.10 Hz), 2.39–2.34 (2H, m), 2.04–1.99 (2H, m). LCMS calcd for C11H13N2O2S (M+H): 237.29; found: 237.26.

Workup

  1. stirringthe resulting mixture was stirred at 80° C. for 18 h
  2. temperaturecooled
  3. filtrationthe resulting solid filtered
  4. concentrationThe mother liquor was concentrated
  5. customthe residue was recrystalized from 1:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e17c4ea10ce440a9a94f4f6d840ce46b
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

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