Tetrahydrofuran → HCID 58465606, compound

HRID 1842459Notes

Reaction equation

HRID 1842459 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:17][C:18]#[CH:19])[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])(=[O:7])=[O:6].[N+:20](=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N-:21].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCCC1>C1C=CC=CC=1>[N+:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[S:5]([N:4]1[CH2:3][CH2:2][N:21]2[N:20]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:19]=[C:18]2[CH2:17]1)(=[O:7])=[O:6])([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 12192Ethyl diazoacetateHCID 57517459HCID 57517459, compound

Product 1

HCID 58465606HCID 58465606, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of N-(2-chloroethyl)-2-nitro-N-(prop-2-yn-1-yl)benzenesulfonamide (0.51 g, 1.69 mmol and ethyl diazoacetate (0.266 mL, 2.532 mmol) in benzene (2 mL) was heated in a microwave reactor at 140° C. for 1 hour. Upon cooling to room temperature, cesium carbonate (0.637 g, 1.95 mmol) along with tetrahydrofuran (1 mL) was added. The vial was again sealed and heated at 140° C. for 30 minutes in the microwave reactor. Upon cooling to room temperature, the solvents were then evaporated in vacuo 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 16 as a semi solid (0.235 g, 37%). LC-MS: (FA) ES+381; 1H NMR (400 MHz, CDCl3) δ 8.07 (dd, J=7.5, 1.7 Hz, 1H), 7.79-7.67 (m, 3H), 6.63 (s, 1H), 4.64 (s, 2H), 4.41-4.31 (m, 4H), 3.92-3.89 (m, 2H), 1.37 (t, J=7.1 Hz, 3H).

Workup

  1. customThe vial was again sealed
  2. temperatureheated at 140° C. for 30 minutes in the microwave reactor
  3. temperatureUpon cooling to room temperature
  4. customthe solvents were then evaporated in vacuo
  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-06b207798d874f9cabcd7df91fba62de
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

Loading…