N-Hydroxyphthalimide → HCID 14207366, compound

HRID 1649373Notes

Reaction equation

HRID 1649373 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[S:13]1[CH2:16][CH:15]([OH:17])[CH2:14]1.O[N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[S:13]1[CH2:16][CH:15]([O:17][N:19]2[C:20](=[O:29])[C:21]3=[CH:28][CH:27]=[CH:26][CH:25]=[C:22]3[C:23]2=[O:24])[CH2:14]1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 825323-Thietan-1-olHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 14207366HCID 14207366, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Diethyl azodicarboxylate (4.3 g) was added all at once to a stirred mixture of 3-thietanol (2.0 g), N-hydroxyphthalimide (3.6 g) and triphenylphosphine (5.8 g) in dry tetrahydrofuran (100 ml) at room temperature. The temperature of the reaction mixture was raised to 40° C. The mixture became clear solution and was stirred for 12 hours at room temperature. Tetrahydrofuran was evaporated in vacuo and the residue was dissolved in ethyl acetate (50 ml). The insoluble substance was filtered off. The filtrate was washed three times with a saturated aqueous solution of sodium bicarbonate (50 ml) and with a saturated aqueous solution of sodium chloride (50 ml), dried over magnesium sulfate and evaporated. The residue was dissolved in methylene chloride (50 ml), subjected to column chromatography on silica gel and eluted with methylene chloride. The fractions containing the object compound were collected and evaporated in vacuo to give N-(3-thietanyloxy)phthalimide (2.0 g).

Workup

  1. customTetrahydrofuran was evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  3. filtrationThe insoluble substance was filtered off
  4. washThe filtrate was washed three times with a saturated aqueous solution of sodium bicarbonate (50 ml)
  5. dry with materialwith a saturated aqueous solution of sodium chloride (50 ml), dried over magnesium sulfate
  6. customevaporated
  7. dissolutionThe residue was dissolved in methylene chloride (50 ml)
  8. washeluted with methylene chloride
  9. additionThe fractions containing the object compound
  10. customwere collected
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-be933167d70f4ce7abc2755f10f21fec
Source dataset
uspto-grants-1983_11
Patent number
US04416879

Reaction notes

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