Diethyl Ether → Phthalimide

HRID 1441121Notes

Reaction equation

HRID 1441121 reaction equation
S(Cl)(Cl)=[O:2].C([N:7]([CH2:10][CH3:11])CC)C.CC[O:14][CH2:15][CH3:16].O1[CH2:21][CH2:20][CH2:19][CH2:18]1>O1CCOCC1>[C:15]1(=[O:14])[C:16]2[C:11](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10](=[O:2])[NH:7]1

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 24386Thionyl Chloride

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

If the compound of formula IVa is desired, then the diol of formula IX is reacted with thionyl chloride in a known manner in the presence of an organic base, preferably an amine such as an alkylamine, for example, triethylamine or Hu/ nig base, in an organic solvent which is inert under the reaction conditions, such as an ether, for example, diethyl ether, tetrahydrofuran or dioxane, and the like at a temperature between about -15° and 80° C., preferably at about 0° C. A 1:1 mixture of the two 2- (S)-1- (2R,4S)- and (2S,4S)-2-oxo-1,3,2-dioxathiolan-4-yl!isomers -2-phenylethyl!-2,3-dihydro-1H-isoindole-1,3-dione is thus formed.

Workup

  1. customlike at a temperature between about -15° and 80° C.
  2. custompreferably at about 0° C
  3. additionA 1:1 mixture of the two 2- (S)-1- (2R,4S)- and (2S,4S)-2-oxo-1,3,2-dioxathiolan-4-yl

Sources & evidence

ORD record
ord-acd6d326bb0041609376693cf86e1c2f
Source dataset
uspto-grants-1996_03
Patent number
US05502210

Reaction notes

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