2-Mercaptoethanol → HCID 10892964, compound

HRID 1385292Notes

Reaction equation

HRID 1385292 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:19][C:6]2=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[S:8][C:9]([S:10]([CH3:12])=O)=[C:5]2[C:4](=[O:20])[CH2:3]1.[OH-].[Na+].SC[CH2:26][OH:27]>C(O)C.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:21])[CH2:19][C:6]2=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[S:8][C:9]([S:10][CH2:12][CH2:26][OH:27])=[C:5]2[C:4](=[O:20])[CH2:3]1

Participants

6

Reactant 3

HCID 15672-Mercaptoethanol2×HCID 14798Sodium Hydroxide2×HCID 10969232HCID 10969232, compound

Product 1

HCID 10892964HCID 10892964, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

6,6-Dimethyl-3-methanesulphinyl-1-(pyrid-2-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (160 mg, 0.5 mmol) was suspended in ethanol (5 mL) and 4M sodium hydroxide solution (138 μL, 0.55 mmol) was added. 2-Mercaptoethanol (43 mg, 0.55 mmol) was added and the suspension was stirred at 20° C. for 2 h. After this time, further 2-mercaptoethanol (10 mg, 0.12 mmol) and 4M sodium hydroxide solution (35 μL, 0.12 mmol) was added and the mixture stirred for a further 2 h. The mixture was then diluted with ethyl acetate and 1M HCL (1 mL) was added. The ethyl acetate layer was washed with water, dried (Na2SO4), then evaporated to dryness. The residue was purified by chromatographed on silica gel, eluting with ethyl acetate, to yield the title compound as a pale yellow solid (58 mg, 36%). mp 175-177° C. Found: C, 61.18; H, 5.62; N, 3.97%. C17H19NO2S2 requires: C, 61.26; H, 5.70; N, 4.20%. 1HNMR (360 MHz, CDCl3)δ 1.08 (6H, s), 2.45 (2H, s), 2.93 (2H, s), 3.33 (2H, t, J=7.2 Hz), 3.98-4.02 (2H, m), 7.16-7.20 (1H, m), 7.46-7.49 (1H, m), 7.72-7.76 (1H, m), 8.64-8.66 (1H, m). MS (ES+) 334 (M+1).

Workup

  1. stirringthe mixture stirred for a further 2 h
  2. additionwas added
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customThe residue was purified
  7. customby chromatographed on silica gel
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-b554612716664db5b7c380e79e4693a9
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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