Formamide → HCID 1516200, compound

HRID 915680Notes

Reaction equation

HRID 915680 reaction equation
[CH:1]([NH2:3])=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:5].Br[CH2:19][C:20](=O)[CH2:21][CH2:22][N:23]1[C:31](=[O:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]1=[O:33].[OH-].[Na+]>O1CCOCC1.C(OCC)(=O)C>[S:5]1[CH:19]=[C:20]([CH2:21][CH2:22][N:23]2[C:31](=[O:32])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]2=[O:33])[N:3]=[CH:1]1

Participants

7

Reactant 4

HCID 713FormamideHCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 37597442-(4-Bromo-3-oxobutyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 1516200HCID 1516200, compoundYield 39.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Reflux formamide (2 mL, 50 mmol) and P2S5 (4.4 g, 10 mmol) dioxane (50 mL) for 2 hours. Add this crude solution to 2-(4-bromo-3-oxobutyl)isoindole-1,3-dione (2.3 g, 7.7 mmol) in dioxane (100 mL) and reflux the resulting reaction solution for 1.5 hours. Add ethyl acetate (100 mL) and 1N sodium hydroxide (100 mL) to the mixture. Separate the organic phase, wash with brine (50 mL), dry (Na2SO4), filter and concentrate in vacuo to an oil. Perform chromatography (silica gel, 7:3 hexane/ethyl acetate) to afford 2-(2-thiazol-4-ylethyl)isoindole-1,3-dione (790 mg). 1H NMR (CDCl3) δ 8.75 (s, 1H), 7.80-7.88 (m, 2H), 7.69-7.75 (m, 2H), 7.08 (s, 1H), 4.10 (t, J=7 Hz, 2H), 3.28 (t, J=7 Hz, 2H).

Workup

  1. temperaturereflux
  2. customthe resulting reaction solution for 1.5 hours
  3. customSeparate the organic phase
  4. washwash with brine (50 mL)
  5. dry with materialdry (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrate in vacuo to an oil

Sources & evidence

ORD record
ord-4a243b332dd34476a7584aba3d26ef0f
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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