Sodium hydride → 4-(1,1-Dioxo-1lambda6-isothiazolidin-2-yl)-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29310Notes

Reaction equation

HRID 29310 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][S:17]([CH2:20][CH2:21][CH2:22]Cl)(=[O:19])=[O:18])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[H-].[Na+]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([N:16]3[CH2:22][CH2:21][CH2:20][S:17]3(=[O:19])=[O:18])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 687137824-(3-Chloro-propane-1-sulfonylamino)-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 687140664-(1,1-Dioxo-1lambda6-isothiazolidin-2-yl)-3-methyl-benzofuran-2-carboxylic acid ethyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-(3-chloro-propane-1-sulfonylamino)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (246 mg, 0.68 mmol, 1 eq.) in THF (10 mL) cooled to <0° C. was added sodium hydride (60%, 30 mg, 0.75 mmol, 1.1 eq.). The reaction was allowed to slowly warm to room temperature, then transferred to a pressure tube and heated at 74° C. for 16 hours. After work-up and flash column chromatography, 4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-3-methyl-benzofuran-2-carboxylic acid ethyl ester was obtained. Yield: 64%. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.3 (t, J=7.1 Hz, 3 H) 2.5 (m, 2 H) 2.7 (s, 3 H) 3.5 (m, 2 H) 3.7 (dd, J=6.8 Hz, 2 H) 4.4 (q, J=7.1 Hz, 2 H) 7.4 (dd, J=7.8, 0.8 Hz, 1 H) 7.6 (m, 1 H) 7.7 (dd, J=8.3, 0.8 Hz, 1 H).

Workup

  1. customtransferred to a pressure tube
  2. temperatureheated at 74° C. for 16 hours

Sources & evidence

ORD record
ord-3c740a1e494747659e9522660deaf8fc
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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