Diisopropylethylamine → 2-[7-(3,4-Dimethoxyphenyl)-7-[(4-methylphenyl)thio]heptyl]-2,3-dihydro-5,6-dimethoxy-1H-isoindole

HRID 274001Notes

Reaction equation

HRID 274001 reaction equation
Br[CH:2]([CH3:26])[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)[S:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][C:37]=1[O:38][CH3:39])[CH2:34][NH:33][CH2:32]2.C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:25][O:24][C:18]1[CH:17]=[C:16]([CH:7]([S:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:26][N:33]2[CH2:34][C:35]3[C:31](=[CH:30][C:29]([O:28][CH3:27])=[C:37]([O:38][CH3:39])[CH:36]=3)[CH2:32]2)[CH:21]=[CH:20][C:19]=1[O:22][CH3:23]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 190420934-[6-Bromo-1-[(4-methylphenyl)thio]heptyl]-1,2-dimethoxybenzeneHCID 200743515,6-Dimethoxyisoindoline

Product 1

HCID 106976132-[7-(3,4-Dimethoxyphenyl)-7-[(4-methylphenyl)thio]heptyl]-2,3-dihydro-5,6-dimethoxy-1H-isoindoleYield 61.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.79 g of 4-[6-bromo-1-[(4-methylphenyl)thio]heptyl]-1,2-dimethoxybenzene, 3.29 g of 5,6-dimethoxyisoindoline, 25 mL of acetonitrile, and 1.74 mL of N,N-diisopropylethylamine is heated under reflux for 2 days. The reaction is concentrated in vacuo and the black residue partitioned between chloroform and aqueous ammonia. The organic layer is dried (sodium sulfate) and the solvent removed at reduced pressure. Chromatography on silica gel with gradient elution progressing from hexane to chloroform to methyl alcohol, twice, gives 1.34 g of the desired product as a brown gum.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 days
  3. concentrationThe reaction is concentrated in vacuo
  4. customthe black residue partitioned between chloroform and aqueous ammonia
  5. dry with materialThe organic layer is dried (sodium sulfate)
  6. customthe solvent removed at reduced pressure

Sources & evidence

ORD record
ord-c1cbec2578a641d59f0725a28ac28f01
Source dataset
uspto-grants-1995_02
Patent number
US05387685

Reaction notes

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