Sodium methanethiolate → HCID 69513751, compound

HRID 858147Notes

Reaction equation

HRID 858147 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8]C#N)[CH:5]=[C:4]([Cl:11])[C:3]=1[O:12][C:13](=[O:15])[CH3:14].C[S-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([SH:8])[CH:5]=[C:4]([Cl:11])[C:3]=1[O:12][C:13](=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 85849960HCID 85849960, compound

Product 1

HCID 69513751HCID 69513751, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of compound from step (ii) (472 mg, 1.69 mmol) in MeOH (17 mL), a solution of sodium thiomethoxide (130 mg, 1.86 mmol) in MeOH (4 mL) was added at room temperature. The reaction mixture was allowed to stir at rt, under nitrogen atmosphere overnight. Then it was concentrated in vacuo and a 0.1 M solution of HCl (30 mL) and CH2Cl2 were added. The layers were separated and the aqueous phase was extracted with CH2Cl2. The combined organic phase was dried over MgSO4, filtered and CIV to afford 315 mg (79%) of the final compound as a white solid.

Workup

  1. concentrationThen it was concentrated in vacuo
  2. additiona 0.1 M solution of HCl (30 mL) and CH2Cl2 were added
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with CH2Cl2
  5. dry with materialThe combined organic phase was dried over MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-f800b1c009df4735b3b2239d6adfb5af
Source dataset
uspto-grants-2006_12
Patent number
US07148236B2

Reaction notes

Loading…