Sodium methanethiolate → HCID 58758907, compound

HRID 2242522Notes

Reaction equation

HRID 2242522 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[C:4]([Cl:10])[C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.C[S-].[Na+]>CN(C=O)C>[Cl:10][C:4]1[CH:5]=[C:6]([OH:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 58758917HCID 58758917, compound

Product 1

HCID 58758907HCID 58758907, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared in a manner analogous to that of Example 2 Step B, by the reaction of 3.7 grams (0.01 mole) of tert-butyl 4-(2,6-dichloro-4-methoxyphenyl)piperazinecarboxylate and 1.8 grams (0.025 mole) of sodium methanethiolate in 150 mL of DMF. The crude reaction product was purified with column chromatography on silica gel using 50% hexane in methylene chloride, 100% methylene chloride and finally 20% methanol in methylene chloride as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.88 gram of the subject compound. The NMR spectrum was consistent with the proposed structure. The reaction was repeated to obtain additional material for the next reactive step.

Workup

  1. customThis compound was prepared in a manner analogous to that of Example 2 Step B
  2. customThe crude reaction product
  3. customwas purified with column chromatography on silica gel using 50% hexane in methylene chloride, 100% methylene chloride and finally 20% methanol in methylene chloride as eluants
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-42f3e9cdc4284e5dae959f978facb622
Source dataset
uspto-grants-2010_03
Patent number
US07671201B2

Reaction notes

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