Ethyl oxoacetate → Ethyl 2-((tert-butylsulfinyl)imino)acetate

HRID 594414Notes

Reaction equation

HRID 594414 reaction equation
O=[CH:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:8][C:9]([S:12]([NH2:14])=[O:13])([CH3:11])[CH3:10]>C(Cl)Cl>[C:9]([S:12]([N:14]=[CH:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:13])([CH3:11])([CH3:10])[CH3:8]

Participants

4

Reactant 2

HCID 70211Ethyl oxoacetateHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 72998703Ethyl 2-((tert-butylsulfinyl)imino)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 2-oxoacetate (50% solution in toluene; 4.066 g; 20.00 mmol), 2-methylpropane-2-sulfinamide (2.424 g; 20.00 mmol), and 4 angstrom molecular sieves (60 g) in anh. DCM (250 ml) was stirred at rt, under nitrogen, for 65 h. The reaction mixture was then filtered over celite, and the separated solids were washed with AcOEt (3×200 ml). The filtrate was then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording ethyl 2-((tert-butylsulfinyl)imino)acetate as a yellow oil.

Workup

  1. filtrationThe reaction mixture was then filtered over celite
  2. washthe separated solids were washed with AcOEt (3×200 ml)
  3. dry with materialThe filtrate was then dried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e539e16197a64c259698f93b40129b4d
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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