Sodium Carbonate → HCID 68703381, compound

HRID 1175185Notes

Reaction equation

HRID 1175185 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH:9]=[CH:8][C@H:7]2[O:11][C:12]([NH2:14])=[N:13][C@@H:6]12)=[O:4].C([O-])([O-])=O.[Na+].[Na+]>CS(C)=O>[CH3:1][O:2][C:3](=[O:4])[NH:5][CH2:10][CH:9]=[CH:8][C:7]1[O:11][C:12]([NH2:14])=[N:13][CH:6]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 11528520HCID 11528520, compound

Product 1

HCID 68703381HCID 68703381, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of product 5 (1.2 g, 6.1 mmol, 0.08M) in DMSO (75.5 ml) is heated at 175° C. for 1 h 30. After cooling at ambient temperature, the reaction mixture is poured onto water (200 ml), basified (5% Na2CO3) to a pH of greater than 10 and then extracted with DCM (4×150 ml). The aqueous phase is then saturated with NaCl and then extracted with DCM (4×150 ml). The organic phases are combined, dried (MgSO4) and then evaporated. The crude product obtained (6.6 g) is then purified by chromatography on silica gel (DCM (sat. NH3) and then DCM (sat. NH3)/MeOH, 98/2). Product 18 (Rf=0.36, DCM/MeOH(NH3): 98/2) is obtained in the form of a brown semisolid (265 mg, 22%), an inseparable mixture of Z/E (14:86) isomers.

Workup

  1. additionthe reaction mixture is poured onto water (200 ml)
  2. extractionextracted with DCM (4×150 ml)
  3. extractionsaturated with NaCl and then extracted with DCM (4×150 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product obtained (6.6 g)
  7. customis then purified by chromatography on silica gel (DCM (sat. NH3)

Sources & evidence

ORD record
ord-fc12561b5b3a4036b92c2adb8cd579a7
Source dataset
uspto-grants-2010_11
Patent number
US07838681B2

Reaction notes

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