Triethylamine → HCID 54067563, compound

HRID 1872868Notes

Reaction equation

HRID 1872868 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:6](=O)(=O)[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.CCN(CC)CC.[CH2:25]([N:27]([CH2:31][CH3:32])[C:28](Cl)=[S:29])[CH3:26]>CCOC(C)=O>[CH2:25]([N:27]([CH2:31][CH3:32])[C:28](=[S:29])[O:1][C:2]1[CH:3]=[CH:4][C:5]2[S:6][C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66607Diethylthiocarbamoyl chlorideHCID 18687760HCID 18687760, compound

Product 1

HCID 54067563HCID 54067563, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-hydroxyphenoxathiin (310 mg, 1.43 mmol) (Example 7), Et3N (0.30 ml, 2.15 mmol) and N,N-diethylthiocarbamoyl chloride (238 mg, 1.57 mmol) in EtOAc (25 mL) was refluxed for 3 h, cooled to room temperature and the precipitated hydrochloride salt filtered. The filtrate was washed with 10% aqueous HCl (30 mL), saturated aqueous NaHCO3 (30 mL) and brine (30 mL), dried (Na2SO4), and concentrated in vacuo to an orange oil (479 mg). The crude product was purified by radial chromatography (EtOAc/hexane 10:90) to give 282 mg (66%) of the title compound as a white solid: mp 121-123° (EtOAc); TLC (EtOAc/hexane, 15:85) Rf =0.43; 1H-NMR (CDCl3) δ 1.32 (=7Hz, 6H), δ 3.68 (q. J=7 Hz, 2 H), δ 3.90 (q, J=7 Hz, 2 H), δ 6.75 (d, J=6 Hz, 1 H, C2 -H), δ 6.78 (s, 1 H, C4 -H), δ 6.95-7.13 (m, 5H): MS m/e (relative intensity) 332 (MH+, 100), 116 (22).

Workup

  1. filtrationthe precipitated hydrochloride salt filtered
  2. washThe filtrate was washed with 10% aqueous HCl (30 mL), saturated aqueous NaHCO3 (30 mL) and brine (30 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo to an orange oil (479 mg)
  5. customThe crude product was purified by radial chromatography (EtOAc/hexane 10:90)

Sources & evidence

ORD record
ord-221a346536bd486cb4ba66053f738125
Source dataset
uspto-grants-2000_08
Patent number
US06110961

Reaction notes

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