Sodium methanethiolate → HCID 90280232, compound

HRID 2170392Notes

Reaction equation

HRID 2170392 reaction equation
[Cl:1][C:2]1[C:3]([C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])=[N:4][CH:5]=[C:6](Cl)[N:7]=1.[CH3:15][S-:16].[Na+]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:3]([C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])=[N:4][CH:5]=[C:6]([S:16][CH3:15])[N:7]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolate2×HCID 90280317HCID 90280317, compound

Product 1

HCID 90280232HCID 90280232, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 55B (2 g, 8.47 mmol) in DMF (10 mL), 1 eq. of sodium methanethiolate was added to the solution. After 5 hours, 0.5 eq. of sodium methanethiolate was added to the suspension. The reaction was stirred overnight then diluted with EtOAc and washed with NaHCO3 (aq) and brine. The organic layer was concentrated and purified by flash chromatography to provide the title compound. MS (m/z) 248 [M+H]+.

Workup

  1. washwashed with NaHCO3 (aq) and brine
  2. concentrationThe organic layer was concentrated
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-d7f1243286a64fb4875dd08c5048bab7
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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