Ammonium Chloride → Ethyl 2-(2,6-dimethoxyphenyl)-2-(1,1-dimethylethylsulfinamido)-acetate

HRID 594407Notes

Reaction equation

HRID 594407 reaction equation
I[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:10][CH3:11].[Li]CCCC.[C:17]([S:21]([N:23]=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:22])([CH3:20])([CH3:19])[CH3:18].[NH4+].[Cl-]>C1COCC1.CCOCC.O>[CH3:11][O:10][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH3:9])[C:2]=1[CH:24]([NH:23][S:21]([C:17]([CH3:18])([CH3:20])[CH3:19])=[O:22])[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 113914072-Iodo-1,3-dimethoxybenzeneHCID 72998703Ethyl 2-((tert-butylsulfinyl)imino)acetateHCID 178418339Butyllithium

Product 1

HCID 69084952Ethyl 2-(2,6-dimethoxyphenyl)-2-(1,1-dimethylethylsulfinamido)-acetate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A cooled (−78° C.) solution of 2-iodo-1,3-dimethoxybenzene (4.119 g; 15.13 mmol) in anh. THF (40 ml) was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (10.40 ml; 16.64 mmol), and the resulting mixture was stirred at −78° C., under nitrogen, for 10 min. A solution of ethyl 2-((tert-butylsulfinyl)imino)acetate (3.106 g; 15.13 mmol) in anh. THF (20 ml) was added dropwise, and stirring at −78° C. was then continued for 25 min. The reaction mixture was treated with aq. sat. NH4Cl (30 ml), water (40 ml), and Et2O (60 ml). The separated aq. layer was extracted with Et2O (2×50 ml), and the mixed organic layers were washed with brine (40 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=20/1) afforded ethyl 2-(2,6-dimethoxyphenyl)-2-(1,1-dimethylethylsulfinamido)acetate as a yellow oil. LC-MS (conditions D): tR=0.91 min.; [M+H]+: 344.45 g/mol.

Workup

  1. stirringstirring at −78° C.
  2. waitwas then continued for 25 min
  3. extractionThe separated aq. layer was extracted with Et2O (2×50 ml)
  4. washthe mixed organic layers were washed with brine (40 ml)
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification by FC (DCM/MeOH=20/1)

Sources & evidence

ORD record
ord-1cbbd0e6bf3a4d13bb29fba1a8cb8837
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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