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

HRID 863891Notes

Reaction equation

HRID 863891 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. MS(Hi res): m/z Calcd for C32H41NO4S 535.2756 Found 535.2723 Calcd for C32H41NO4S H2O C=69.41, H=7.83, N=2.53, S=5.78 Found C=69.59, H=7.51, N=2.53, S=6.19

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-39d9d14fec5f4e08a669d11405cc16fb
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

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