Sodium Hydroxide → HCID 15407424, compound

HRID 1274301Notes

Reaction equation

HRID 1274301 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.[OH-].[Na+].[F:26][C:27]([F:31])([F:30])CS>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][CH2:13][C:27]([F:31])([F:30])[F:26])=[C:5]2[C:4](=[O:22])[CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 41339242,2,2-TrifluoroethanethiolHCID 15407420HCID 15407420, compound

Product 1

HCID 15407424HCID 15407424, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 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 NaOH (0.7 mL of a 3 M solution, 2.3 mmol) followed by 2,2,2-trifluoroethanethiol (0.2 mL, 2.2 mmol). The mixture was stirred at room temperature for 3 h then evaporated. The residue was partitioned between EtOAc (20 mL) and NaOH (1M; 30 mL). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was triturated with ether and the colourless solid (166 mg, 35%) collected by filtration. C17H20F3NO2S2 requires: C, 52.16; H, 5.15; N, 3.58%. Found: C, 51.86; H, 4.99; N, 3.61%. 1H NMR (360 MHz, CDCl3) δ 1.05 (6H, s), 1.95-1.99 (4H, m), 2.42 (2H, s), 2.86 (2H, s), 3.57-3.63 (4H, m), 3.66 (2H, q, J=9.5 Hz). MS (ES+) 392 (M+1).

Workup

  1. customthen evaporated
  2. customThe residue was partitioned between EtOAc (20 mL) and NaOH (1M; 30 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was triturated with ether
  7. filtrationthe colourless solid (166 mg, 35%) collected by filtration

Sources & evidence

ORD record
ord-69329ac86b214b569cd912c2f94a1c17
Source dataset
uspto-grants-2000_12
Patent number
US06156787

Reaction notes

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