Propyl mercaptan → HCID 22132962, compound

HRID 1856828Notes

Reaction equation

HRID 1856828 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+].[CH2:26](S)[CH2:27]C>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][CH2:26][CH3:27])=[C:5]2[C:4](=[O:22])[CH2:3]1

Participants

5

Reactant 3

HCID 7848Propyl mercaptanHCID 14798Sodium HydroxideHCID 15407420HCID 15407420, compound

Product 1

HCID 22132962HCID 22132962, 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 (500 mg, 1.4 mmol) in EtOH (15 mL) was added NaOH (0.71 mL of a 4 M solution, 2.8 mmol) followed by propanethiol (255 μL, 2.8 mmol). The mixture was stirred at room temperature for 2 h then evaporated. The residue was partitioned between EtOAc (20 mL) and water (20 mL). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was triturated with ether and the colourless solid (380 mg, 77%) collected by filtration. mp 117-119° C. C18H25NO2S2 requires: C, 61.50; H, 7.17; N, 3.98%. Found: C, 61.48; H, 7.02; N, 3.97%. 1H NMR (250 MHz, CDCl3) δ1.04 (6H, s), 1.10 (3H, t, J=7.3 Hz), 1.87 (2H, sextet, J=7.3 Hz), 1.93-1.99 (4H, m), 2.40 (2H, s), 2.83 (2H, s), 3.00 (2H, t, J=7.3 Hz), 3.57-3.63 (4H, m). MS (ES+) 352 (M+1).

Workup

  1. customthen evaporated
  2. customThe residue was partitioned between EtOAc (20 mL) and water (20 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 (380 mg, 77%) collected by filtration

Sources & evidence

ORD record
ord-9ae69c47f29846aeb6582afeb16cf710
Source dataset
uspto-grants-2000_11
Patent number
US06143773

Reaction notes

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