Water → HCID 118098706, compound

HRID 708833Notes

Reaction equation

HRID 708833 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[CH:23](C(OCC)=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Li+].O>CS(C)=O.CCOC(C)=O>[CH2:1]([O:8][C:9]([N:11]([CH2:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:12])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 118101242HCID 118101242, compound

Product 1

HCID 118098706HCID 118098706, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

10A (3.22 g, 7.02 mmol) was dissolved in DMSO (25 mL), lithium chloride (0.596 g, 14.05 mmol) and water (0.152 mL, 8.43 mmol) were added. The reaction mixture was stirred at 130° C. for 3 h, then was cooled to rt, diluted with EtOAc (250 mL), washed with water (2×100 mL), brine (1×100 mL) and dried (Na2SO4). EtOAc was removed under reduced pressure and the crude product was purified by flash chromatography to give 10B (850 mg, 31.3% yield); MS (ESI) m/z: 386.9 (M+H)+.

Workup

  1. temperaturewas cooled to rt
  2. washwashed with water (2×100 mL), brine (1×100 mL)
  3. dry with materialdried (Na2SO4)
  4. customEtOAc was removed under reduced pressure
  5. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-ef18f1c455cb4b6a84e1458bf6401d8d
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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