HCID 15407420, compound → HCID 15407421, compound

HRID 1856827Notes

Reaction equation

HRID 1856827 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:21][C:6]2=[C:7]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[S:8][C:9]([S:10]([CH3:13])(=O)=O)=[C:5]2[C:4](=[O:22])[CH2:3]1.[Na].[C:25]1(S)[CH:30]=[CH:29]C=[CH:27][CH:26]=1>CCO>[CH3:1][C:2]1([CH3:23])[CH2:21][C:6]2=[C:7]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[S:8][C:9]([S:10][C:13]3[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=3)=[C:5]2[C:4](=[O:22])[CH2:3]1

Participants

4

Reactant 2

HCID 15407420HCID 15407420, compoundHCID 66586497Sodium benzenethiol

Product 1

HCID 15407421HCID 15407421, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of the 6,6-dimethyl-3-methanesulphonyl-1-(pyrrolidin-1-ylcarbonyl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (400 mg, 1.1 mmol) in EtOH (15 mL) was added thiophenol sodium salt (297 mg, 2.2 mmol). The mixture was stirred at room temperature for 3 h then the solvent evaporated. The residue was partitioned between EtOAc (20 mL) and water (30 mL). The organic phase was separated, dried (Na2SO4) and evaporated. The resultant oil was triturated with ether/hexane and the colourless solid (330 mg, 76%) collected by filtration. mp 140° C. C21H23NO2S2 requires: C, 65.42; H, 6.01; N, 3.63%. Found: C, 65.55; H, 5.77; N, 3.980%,. 1H NMR (360 MHz, CDCl3) δ1.07 (6H, s), 1.86-1.90 (4H, m), 2.43 (2H, s), 2.78 (2H, s), 3.36-3.60 (4H, m), 7.43-7.51 (3H, m), 7.67-7.70 (2H, m). MS (ES+) 386 (M+1).

Workup

  1. customthe solvent evaporated
  2. customThe residue was partitioned between EtOAc (20 mL) and water (30 mL)
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe resultant oil was triturated with ether/hexane
  7. filtrationthe colourless solid (330 mg, 76%) collected by filtration

Sources & evidence

ORD record
ord-d931dfe367be4e7e828957a5bbc40269
Source dataset
uspto-grants-2000_11
Patent number
US06143773

Reaction notes

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