Methanol → HCID 20032352, compound

HRID 231432Notes

Reaction equation

HRID 231432 reaction equation
[Cl:1][C:2]1[C:7](CO)=[CH:6][C:5]([N:10]2[C:14](=[O:15])[C:13]3[CH2:16][CH2:17][CH2:18][CH2:19][C:12]=3[C:11]2=[O:20])=[C:4]([F:21])[CH:3]=1.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.C[OH:39]>C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([O:30][C:29]([NH:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:39])=[CH:6][C:5]([N:10]2[C:14](=[O:15])[C:13]3[CH2:16][CH2:17][CH2:18][CH2:19][C:12]=3[C:11]2=[O:20])=[C:4]([F:21])[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7672Phenyl isocyanate2×HCID 8471TriethylamineHCID 136297542-[4-Chloro-2-fluoro-5-(hydroxymethyl)phenyl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione

Product 1

HCID 20032352HCID 20032352, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.5 g (0.0016 mole) of N-(4-chloro-2-fluoro-5-hydroxymethylphenyl]-3,4,5,6-tetrahydrophthalimide, 0.66 g (0.0055 mole) of phenyl isocyanate, 0.73 g (0.0072 mole) of triethylamine, and 25 ml of methylene was stirred at room temperature overnight. Sufficient methanol was added to react with the excess phenyl isocyanate, and the reaction mixture was stirred for an additional 24 hours. The reaction mixture was diluted with ethyl acetate and was washed successively with water and 5% hydrochloric acid. The organic phase was dried, filtered, and the solvent was evaporated under reduced pressure. The residue was passed through a column of silica gel. The appropriate fractions were combined, and the solvent was evaporated under reduced pressure, leaving a white solid as a residue. This solid was recrystallized from ethyl acetate/heptane, yielding 0.29 g of N-[4-chloro-2-fluoro-5-(phenylaminocarbonyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide as a white solid, m.p. 149°-151° C. The nmr and ir spectra were consistent with the proposed structure.

Workup

  1. stirringthe reaction mixture was stirred for an additional 24 hours
  2. washwas washed successively with water and 5% hydrochloric acid
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customthe solvent was evaporated under reduced pressure
  7. customleaving a white solid as a residue
  8. customThis solid was recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-afeb54faef7449ceaa56a1c6621796f7
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

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