Lawesson's reagent → HCID 10225223, compound

HRID 478903Notes

Reaction equation

HRID 478903 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([NH:16][CH2:17][C:18](=O)[C:19]3[CH:28]=[CH:27][C:22]4[NH:23][C:24](=[O:26])[S:25][C:21]=4[CH:20]=3)=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:41]2)=CC=1>O1CCOCC1.CCOC(C)=O>[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[S:41][C:18]([C:19]4[CH:28]=[CH:27][C:22]5[NH:23][C:24](=[O:26])[S:25][C:21]=5[CH:20]=4)=[CH:17][N:16]=3)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 87949Lawesson's reagent2×HCID 18002811HCID 18002811, compound

Product 1

HCID 10225223HCID 10225223, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-[4-(4-fluorobenzyl)piperidin-1-yl]-N-[2-oxo-2-(2-oxo-2,3-dihydrobenzothiazol-6-yl)ethyl]acetamide (0.50 g, 1.13 mmol) in 1,4-dioxan (30 mL) was added [2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide] (Lawesson's reagent) (0.69 g, 1.70 mmol). The resulting suspension was heated at reflux for 24 hours. The reaction mixture was condensed to dryness in vacuo, redissolved in EtOAc, and washed with saturated aqueous sodium hydrogen carbonate, and saturated brine. The organic phase was dried (MgSO4) and condensed to dryness in vacuo. The material was then subject to column chromatography [silica gel, EtOAc/Heptanes (0-50% EtOAc over 60 min)] gave 6-{2-[4-(4-fluorobenzyl)piperidin-1-ylmethyl]thiazol-5-yl}-3H-benzothiazol-2-one (0.087 g, 18%) as an off-white solid:

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for 24 hours
  3. customcondensed to dryness in vacuo
  4. washwashed with saturated aqueous sodium hydrogen carbonate, and saturated brine
  5. customThe organic phase was dried
  6. custom(MgSO4) and condensed to dryness in vacuo

Sources & evidence

ORD record
ord-f89f8ace94ad463c90441994c7551fb6
Source dataset
uspto-grants-2003_11
Patent number
US06642256B2

Reaction notes

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