4'-Mercaptoacetanilide → HCID 21874866, compound

HRID 723641Notes

Reaction equation

HRID 723641 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Li]CCCC.Br[CH2:18][CH2:19][C:20]1[O:21][C:22]([CH3:25])=[CH:23][CH:24]=1>C1COCC1>[CH3:25][C:22]1[O:21][C:20]([CH2:19][CH2:18][S:11][C:8]2[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 707774'-MercaptoacetanilideHCID 21875094HCID 21875094, compoundHCID 178418339Butyllithium

Product 1

HCID 21874866HCID 21874866, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 4-acetamidothiophenol (442 mg, 2.64 mmol) in THF (1 mL) at 0° C. under inert atmosphere was added a solution of n-BuLi (2.00 mL, 3.17 mmol, 1.6 M in hexanes) in THF (1 mL). The reaction solution was stirred at room temperature for 10 min then a solution of compound 21B (500 mg, 2.64 mmol) in THF (3 mL) was added. After the starting material was consumed (as determined by TLC), the reaction was quenched with H2O and the mixture was extracted with EtOAc (2×), dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with 50% EtOAc/hexanes gave 0.644 g (2.34 mmol, 88%) of compound 21C. MS (ESI): m/z 276.09 [M+H]+.

Workup

  1. customAfter the starting material was consumed (as determined by TLC)
  2. customthe reaction was quenched with H2O
  3. extractionthe mixture was extracted with EtOAc (2×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography on silica gel eluting with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-2d4b9004f4c24d8e80e7d381bf5a9f5f
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Reaction notes

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