Ethanethiol → HCID 20689153, compound

HRID 495966Notes

Reaction equation

HRID 495966 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[CH2:12][C:11]2[CH:13]=[CH:14][C:15]([O:17]C)=[CH:16][C:10]=2[O:9][C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]1=2)[CH3:2].C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[CH2:12][C:11]2[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:10]=2[O:9][C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]1=2)[CH3:2]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 20689154HCID 20689154, compound

Product 1

HCID 20689153HCID 20689153, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-5 (400 mg, 1.27 mmol) in dichloromethane (5 mL) was cooled to −5° C. and treated with ethanethiol (419 mg, 6.75 mmol) and aluminum chloride (815 mg, 6.11 mmol). After 30 min, the reaction was quenched with aqueous ammonium chloride solution. The solvent was removed in vacuo and the residue dissolved in 1M HCl. The aqueous layer was extracted with three portions of dichloromethane and the combined organic extracts were washed with brine and dried (Na2SO4). The solvent was removed in vacuo. Preparative centrifugal chromatography (SiO2, 4 mm, 10% EtOH; 90% CH2C2) afforded 1-6.

Workup

  1. customthe reaction was quenched with aqueous ammonium chloride solution
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in 1M HCl
  4. extractionThe aqueous layer was extracted with three portions of dichloromethane
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was removed in vacuo
  8. customPreparative centrifugal chromatography (SiO2, 4 mm, 10% EtOH; 90% CH2C2) afforded 1-6

Sources & evidence

ORD record
ord-b1fe33bc22124fb2bce86239b5e28b70
Source dataset
uspto-grants-2005_09
Patent number
US06943156B2

Reaction notes

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