3a,4,5,7a-Tetrahydro-2-benzofuran-1,3-dione → N-[4-chloro-2-fluoro-5-(diisopropylaminomethyl)phenyl]-3,4,5,6-tetrahydrophthalimide

HRID 231439Notes

Reaction equation

HRID 231439 reaction equation
[Cl:1][C:2]1[C:8]([CH2:9][N:10]([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:13])[CH3:12])=[CH:7][C:5]([NH2:6])=[C:4]([F:17])[CH:3]=1.[C:18]1(=O)[O:23][C:21](=[O:22])[CH:20]2[CH2:24][CH2:25][CH:26]=[CH:27][CH:19]12>C(O)(=O)C>[Cl:1][C:2]1[C:8]([CH2:9][N:10]([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:12])[CH3:13])=[CH:7][C:5]([N:6]2[C:21](=[O:22])[C:20]3[CH2:24][CH2:25][CH2:26][CH2:27][C:19]=3[C:18]2=[O:23])=[C:4]([F:17])[CH:3]=1

Participants

4

Reactant 2

HCID 127266013a,4,5,7a-Tetrahydro-2-benzofuran-1,3-dioneHCID 197395974-Chloro-2-fluoro-5-(diisopropylaminomethyl)aniline

Product 1

HCID 20032355N-[4-chloro-2-fluoro-5-(diisopropylaminomethyl)phenyl]-3,4,5,6-tetrahydrophthalimideYield 6.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

By the method of Example 2, Step H, 0.50 g (0.0020 mole) of 4-chloro-2-fluoro-5-(diisopropylaminomethyl)aniline and 0.85 g (0.0056 mole) of tetrahydrophthalic anhydride in 20 ml of acetic acid were reacted yielding 0.052 g of N-[4-chloro-2-fluoro-5-(diisopropylaminomethyl)phenyl]-3,4,5,6-tetrahydrophthalimide. The nmr and ir spectra were consistent with the proposed structure.

Sources & evidence

ORD record
ord-718b691cedde4433b747b2e13c0097aa
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

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