Tetrahydrofuran → HCID 14653123, compound

HRID 1608138Notes

Reaction equation

HRID 1608138 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[N:5]([N:23]([C:27]([O:29]C(C)C)=O)[C:24](=[O:26])[CH:25]=2)[CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:7]=1[C:8]([O:10]C(C)C)=[O:9].[CH2:33]([N:36]=C=O)[CH2:34][CH3:35].O1C[CH2:42][CH2:41][CH2:40]1>N1C=CC=CC=1>[CH3:1][C:2]1[NH:3][C:4]2[N:5]([N:23]([C:27]([NH:36][CH2:33][CH2:34][CH3:35])=[O:29])[C:24](=[O:26])[CH:25]=2)[CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:7]=1[C:8]([O:10][CH:41]([CH3:42])[CH3:40])=[O:9]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 61033Propyl isocyanateHCID 14653121HCID 14653121, compound

Product 1

HCID 14653123HCID 14653123, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The suspension of the title A compound from Example 1 (0.75 g, 2.0 mmol) in tetrahydrofuran (10 mL) and pyridine (1 mL) was treatetd at 0° C. under argon with n-propylisocyanate (0.24 mL, 2.5 mmol). After the addition was finished, the cooling bath was removed and the reaction was allowed to stir at room temperature for 5 hours. The resulting solution was diluted with ethyl acetate and was washed with 1N hydrochloric acid, water and brine. After drying over anhydrous magnesium sulfate, the solvent was removed and the residue was crystallized from ether-hexanes to yield 701 mg of a colorless solid. The product was recrystallized from dichloromethane-isopropyl ether to yield 601 mg of the title compound, m.p. 160°-163° C.

Workup

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. additionThe resulting solution was diluted with ethyl acetate
  4. washwas washed with 1N hydrochloric acid, water and brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customthe residue was crystallized from ether-hexanes

Sources & evidence

ORD record
ord-f01a1989996a4f2182338e5b4b70f916
Source dataset
uspto-grants-1989_09
Patent number
US04870072

Reaction notes

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