Sodium Sulfide → HCID 86585913, compound

HRID 488381Notes

Reaction equation

HRID 488381 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:11]=[CH:12][C:13]=1[CH2:14][CH2:15]OS(C)(=O)=O)(=O)=O.[S-2:32].[Na+].[Na+]>CS(C)=O>[CH2:14]1[C:13]2[CH:12]=[CH:11][C:10]([NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:9][C:8]=2[CH2:7][CH2:6][S:32][CH2:15]1

Participants

4

Reactant 2

HCID 14804Sodium SulfideHCID 86585914HCID 86585914, compound

Product 1

HCID 86585913HCID 86585913, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of the bis mesylate (from step 4) (5.0 g, 10.6 mmol) in dry DMSO (72 mL) is added anhydrous sodium sulfide (2.48 g, 31.8 mmol). The reaction mixture is stirred at RT for 1 h. The reaction mixture is partitioned between H2O (250 mL) and ethyl acetate (250 mL). The phases are separated, the aqueous phases is extracted with ethyl acetate (3×200 mL). The combined organic phases are dried (MgSO4), filtered and concentrated. The residue is dissolved in CH2Cl2, absorbed onto silica gel and is purified on a Biotage 40M column with SIM using 10-20% ethyl acetate in hexane as the eluent to afford 2.37 g (7.6 mmol, 71%) of the desired product as a white solid. mp 118-120° C.

Workup

  1. customThe reaction mixture is partitioned between H2O (250 mL) and ethyl acetate (250 mL)
  2. customThe phases are separated
  3. extractionthe aqueous phases is extracted with ethyl acetate (3×200 mL)
  4. dry with materialThe combined organic phases are dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue is dissolved in CH2Cl2
  8. customabsorbed onto silica gel
  9. customis purified on a Biotage 40M column with SIM

Sources & evidence

ORD record
ord-0b98c7a762c047e9b5208c255b01e5c6
Source dataset
uspto-grants-2005_12
Patent number
US06972286B2

Reaction notes

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