Dicyclohexylamine → 1H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-(1-methylethoxy)phenyl)-4,5,6,7-tetrahydro-

HRID 1284608Notes

Reaction equation

HRID 1284608 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:4][C:3]=1[N:12]1[C:16](=[O:17])[C:15]2[CH2:18][CH2:19][CH2:20][CH2:21][C:14]=2[C:13]1=[O:22].C1(NC2CCCCC2)CCCCC1.[Cl:36]Cl>ClC(Cl)=C(Cl)Cl>[Cl:36][C:6]1[C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:4][C:3]([N:12]2[C:13](=[O:22])[C:14]3[CH2:21][CH2:20][CH2:19][CH2:18][C:15]=3[C:16]2=[O:17])=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 7582DicyclohexylamineHCID 24526ChlorineHCID 13556385N-(2-Fluoro-5-isopropoxyphenyl)-3,4,5,6-tetrahydrophthalimide

Product 1

HCID 1586501H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-(1-methylethoxy)phenyl)-4,5,6,7-tetrahydro-

Reagents, catalysts & solvents 1

HCID 31373TetrachloroethyleneSolvent

Procedure

N-(2-Fluoro-5-isopropoxyphenyl)-3,4,5,6-tetrahydrophthalimide (II: R=isopropyl) (1 g) and dicyclohexylamine (0.01 g) were dissolved in tetrachloroethylene (20 ml), and chlorine (1 ml) was introduced therein at room temperature. The resultant solution was stirred at the room temperature for 2 hours. The reaction mixture was extracted with methylene chloride, and the extract was concentrated. The residue was purified by silica gel chromatography using a mixture of n-hexane and ethyl acetate as an eluent to give 0.9 g of N-(4-chloro-2-fluoro-5-isopropoxyphenyl)-3,4,5,6-tetrahydrophthalimide (I: R=isopropyl). M.P., 81°-82° C.

Workup

  1. customat room temperature
  2. extractionThe reaction mixture was extracted with methylene chloride
  3. concentrationthe extract was concentrated
  4. customThe residue was purified by silica gel chromatography
  5. additiona mixture of n-hexane and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-894856193b0b4e4591cd2b42f6d0931c
Source dataset
uspto-grants-1986_01
Patent number
US04563535

Reaction notes

Loading…