Water → HCID 11139347, compound

HRID 967397Notes

Reaction equation

HRID 967397 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19])C(OCC)=O)[CH3:2].[Li+].[Cl-].O>CS(C)=O>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19])[CH3:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 433294Lithium ChlorideHCID 123156722-(5-Chloro-2-nitro-phenyl)-malonic acid diethyl ester

Product 1

HCID 11139347HCID 11139347, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

2-(5-Chloro-2-nitro-phenyl)-malonic acid diethyl ester (10.3 g, 32.6 mmol) in DMSO (200 mL) containing LiCl (2.9 g, 68.4 mmol) and water (0.6 mL, 33.3 mmol) was set stirring and heated to 100° C. After 5 h the mixture was cooled to room temperature and added to water (750 mL). The product was extracted with two portions of EtOAc. The organics were combined, washed with water, dried (MgSO4) and evaporated to give 5.9 g (75%) of a clear yellow oil. TLC (silica, 25% EtOAc/hexanes): Rf=0.50. 1H NMR (400 MHz, CDCl3): 8.21 (d, J=8.8 Hz, 1H), 7.56 (dd, J=8.8, 2.3 Hz, 2H), 7.47 (d, J=2.3 Hz, 1H), 4.30 (q, J=7.2 Hz, 2H), 4.12 (s, 2H), 1.38 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureAfter 5 h the mixture was cooled to room temperature
  2. extractionThe product was extracted with two portions of EtOAc
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-c8eaf728db3d4fdcaa6d34450eb23290
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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