Diisopropylethylamine → 2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methylsulfanyl-benzyl)-N-methoxy-acetamide

HRID 2214686Notes

Reaction equation

HRID 2214686 reaction equation
Cl.[F:2][C:3]1[CH:12]=[CH:11][C:6]([CH2:7][NH:8][O:9][CH3:10])=[C:5]([S:13][CH3:14])[CH:4]=1.[CH3:15][C:16]1([CH3:26])[O:20][C:19](=[CH:21][C:22](Cl)=[O:23])[C:18](=[O:25])[O:17]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:15][C:16]1([CH3:26])[O:20][C:19](=[CH:21][C:22]([N:8]([CH2:7][C:6]2[CH:11]=[CH:12][C:3]([F:2])=[CH:4][C:5]=2[S:13][CH3:14])[O:9][CH3:10])=[O:23])[C:18](=[O:25])[O:17]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 21947459N-(4-fluoro-2-methylsulfanyl-benzyl)-O-methyl-hydroxylamine hydrochlorideHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 738555662-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methylsulfanyl-benzyl)-N-methoxy-acetamideYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(4-fluoro-2-methylsulfanyl-benzyl)-O-methyl-hydroxylamine hydrochloride (1.19 g, 5 mmol) and (2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride (0.953 g, 5 mmol) in CH2Cl2 (20 mL) was added diisopropyethylamine (1.9 mL, 11 mmol) at room temperature. After 1 h, the reaction mixture was concentrated and the resulting residue was taken up into ether (150 mL), washed with 1N HCl (10 mL), water (20 mL) and brine (20 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated to give product as a white solid (1.77 g, 99%). 1HNMR (300 MHz, CDCl3) δ: 7.28–7.23 (1H, m), 6.90 (1H, dd, J=9.5, 2.6 Hz), 6.78 (1H, td, J=8.4, 2.6 Hz), 6.37 (1H, s), 4.88 (2H, s), 3.62 (3H, s), 2.44 (3H, s), 1.71 (6H, s). MS calcd for C16H18FNO5S Na (M+Na): 378.078; found: 378.18.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. washwashed with 1N HCl (10 mL), water (20 mL) and brine (20 mL)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cf72be67142f43acae7984f5ccc4c506
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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