Cesium carbonate → HCID 58465583, compound

HRID 1842462Notes

Reaction equation

HRID 1842462 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]([CH2:18][C:19]#[CH:20])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7].[N+:21](=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N-:22].C(N(CC)C(C)C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC=CC=1.O1CCCC1>[N+:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[S:6]([N:5]1[CH2:4][CH2:3][CH2:2][N:22]2[N:21]=[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:20]=[C:19]2[CH2:18]1)(=[O:8])=[O:7])([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 12192Ethyl diazoacetateHCID 81531DiisopropylethylamineHCID 57517460HCID 57517460, compound

Product 1

HCID 58465583HCID 58465583, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of N-(3-chloropropyl)-2-nitro-N-(prop-2-yn-1-yl)benzenesulfonamide (0.5 g, 1.59 mmol) and ethyl diazoacetate (0.251 mL, 2.384 mmol) in benzene (1.5 mL) was added N,N-diisopropylethylamine (0.27 mL, 1.6 mmol). The resulting solution was heated in a microwave reactor at 140° C. for 1 hour. Upon cooling to room temperature, cesium carbonate (0.621 g, 1.91 mmol) and tetrahydrofuran (1 mL) was added and the reaction mixture again heated at 140° C. for 30 minutes. Upon cooling to room temperature, the solvents were evaporated and the residue obtained was partitioned between water (10 mL) and EtOAc (15 mL). The aqueous layer was washed with additional EtOAc (15 mL), the combined organic layers were dried over anhydrous MgSO4, concentrated and purified via silica chromatography (20-90% EtOAc/hexane) to afford Intermediate 19 as a yellow oil (0.314 g, 50%). LC-MS: (FA) ES+395; 1H NMR (400 MHz, CDCl3) δ 7.96 (dd, J=7.8, 1.5 Hz, 1H), 7.73-7.60 (m, 3H), 6.77 (s, 1H), 4.58 (s, 2H), 4.52-4.47 (m, 2H), 4.37 (q, J=7.1 Hz, 2H), 3.72-3.65 (m, 2H), 2.10-2.04 (m, 2H), 1.37 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureUpon cooling to room temperature
  2. temperaturethe reaction mixture again heated at 140° C. for 30 minutes
  3. temperatureUpon cooling to room temperature
  4. customthe solvents were evaporated
  5. customthe residue obtained
  6. customwas partitioned between water (10 mL) and EtOAc (15 mL)
  7. washThe aqueous layer was washed with additional EtOAc (15 mL)
  8. dry with materialthe combined organic layers were dried over anhydrous MgSO4
  9. concentrationconcentrated
  10. custompurified via silica chromatography (20-90% EtOAc/hexane)

Sources & evidence

ORD record
ord-43ef7f96e20643efa535c1df55bc74f0
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

Loading…