Trimethylsilyl cyanide → HCID 90402316, compound

HRID 1854742Notes

Reaction equation

HRID 1854742 reaction equation
C[Si]([C:5]#[N:6])(C)C.[C:7]1(=[N:11][S:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])[CH2:10][CH2:9][CH2:8]1>C(Cl)Cl.CCOC(C)=O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[C:5]([C:7]1([NH:11][S:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])[CH2:8][CH2:9][CH2:10]1)#[N:6]

Participants

6

Reactant 2

HCID 82115Trimethylsilyl cyanide2×HCID 67250305N-cyclobutylidene-2-methylpropane-2-sulfinamide

Product 1

HCID 90402316HCID 90402316, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 76524Titanium tetraethoxideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Titanium (IV) ethoxide (3.03 g, 13.3 mmol) was added to a stirring solution of trimethylsilyl cyanide (7.12 mL, 53.1 mmol) and N-cyclobutylidene-2-methylpropane-2-sulfinamide (4.6 g, 27 mmol) in DCM (100 mL) at rt. The reaction was allowed to stir for 16 h. An additional 1.7 mL of TMS-CN was added followed by 1.5 g of TiOEt4. The reaction was allowed to stir at rt for an additional 16 h. The mixture was diluted with EtOAc and washed with sat NaHCO3, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated to give N-(1-cyanocyclobutyl)-2-methylpropane-2-sulfinamide (4.5 g, 22 mmol, 85% yield) consistent by NMR. 1H NMR (400 MHz, CHLOROFORM-d) δ 2.82-2.67 (m, 2H), 2.62-2.34 (m, 2H), 2.26-2.02 (m, 2H), 1.26 (s, 9H).

Workup

  1. stirringto stir at rt for an additional 16 h
  2. washwashed
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a5957a4adf0a489da4c5161bd818243e
Source dataset
uspto-grants-2015_02
Patent number
US08962651B2

Reaction notes

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