tert-Butyl mercaptan → HCID 28413271, compound

HRID 911753Notes

Reaction equation

HRID 911753 reaction equation
[H-].[Na+].[CH3:3][C:4]([SH:7])([CH3:6])[CH3:5].Br[CH2:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1>CN(C=O)C>[C:4]([S:7][CH2:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1)([CH3:6])([CH3:5])[CH3:3]

Participants

5

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 28413271HCID 28413271, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add sodium hydride (359 mg, 14.21 mmol) to a solution of 2-methyl-2-propanethiol (900 mg, 9.98 mmol) in anhydrous DMF (15 mL) under nitrogen. Stir the mixture for 15 min, add 4-bromomethyl-benzonitrile (2.348 g, 11.97 mmol) and stir the resulting mixture overnight at room temperature. Add water and extract the aqueous phase twice with EtOAc. Wash the combined organic extracts twice with iced-water, dry over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc 92:8 to give the desired intermediate (1.42 g, 69% yield).

Workup

  1. stirringstir the resulting mixture overnight at room temperature
  2. extractionAdd water and extract the aqueous phase twice with EtOAc
  3. washWash the combined organic extracts twice with iced-water
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify by chromatography on silica gel eluting with hexane/EtOAc 92:8

Sources & evidence

ORD record
ord-5bfdedcfa3654c9ca0f64f156523d5f8
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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