Ethanethiol → HCID 67172733, compound

HRID 1256147Notes

Reaction equation

HRID 1256147 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[K+].[K+].[CH3:19][CH2:20][SH:21]>CC#N.O>[CH2:20]([S:21][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1)[CH3:19]

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 18621118HCID 18621118, compound

Product 1

HCID 67172733HCID 67172733, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of N-(3-(bromomethyl)phenyl)acetamide (6.6 g, 29 mmol) in CH3CN (50 mL) and water (10 mL) was added K2CO3 (6 g, 43 mmol) and EtSH (1.79 g, 29 mmol). The mixture was stirred at r.t. overnight. After removal of the solvent, the residue was extracted with EtOAc, dried and concentrated to give the crude product. The crude was purified by silica gel chromatography (petroleum ether:EtOAc=1:0 to 10:1) to give N-(3-(ethylthiomethyl)phenyl)acetamide (3.4 g, 56% yield) as a light yellow solid. 1H NMR: (400 MHz, CDCl3) δ 7.81 (s, 1H), 7.41 (s, 1H), 7.34 (d, 1H), 7.22-7.17 (m, 1H), 7.01 (d, 1H), 3.61 (s, 2H), 2.41-2.34 (m, 2H), 2.11 (s, 3H), 1.24 (t, 3H).

Workup

  1. customAfter removal of the solvent
  2. extractionthe residue was extracted with EtOAc
  3. customdried
  4. concentrationconcentrated
  5. customto give the crude product
  6. customThe crude was purified by silica gel chromatography (petroleum ether:EtOAc=1:0 to 10:1)

Sources & evidence

ORD record
ord-dcf44691b0d1445fa393dd7a4b22533a
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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