Sodium Carbonate → HCID 178502091, compound

HRID 1175186Notes

Reaction equation

HRID 1175186 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH:9]=[CH:8][C@H:7]2[S: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[S:11][C:12](=[NH:14])[NH:13][CH:6]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 11321832HCID 11321832, compound

Product 1

HCID 178502091HCID 178502091, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Compound 6 (0.070 g, 0.32 mmol) is heated in DMSO (5 ml) at 175° C. for 2 h. After cooling to ambient temperature, the reaction mixture is poured onto ice-cold water (100 ml), basified (5% Na2CO3) to a pH of greater than 10 and then extracted with DCM (3×150 ml). The organic phases are combined, washed with saturated NaCl solution, dried (MgSO4) and then evaporated to dryness. The crude product obtained (0.06 g) is then purified by chromatography on thick layers of silica gel (DCM, sat. NH3/MeOH, 95:5). The product (Rf=0.49, DCM/MeOH/NH3 vap., 95:5) is obtained in the form of a brown semisolid (20 mg, 0.09 mmol, 28%), an inseparable mixture of E/Z (9:1) isomers according to 1H NMR.

Workup

  1. additionthe reaction mixture is poured onto ice-cold water (100 ml)
  2. extractionextracted with DCM (3×150 ml)
  3. washwashed with saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe crude product obtained (0.06 g)
  7. customis then purified by chromatography on thick layers of silica gel (DCM, sat. NH3/MeOH, 95:5)

Sources & evidence

ORD record
ord-e0b1d0b884c24496bbd832b8c2e81c4d
Source dataset
uspto-grants-2010_11
Patent number
US07838681B2

Reaction notes

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