Ethanol → HCID 70443678, compound

HRID 247764Notes

Reaction equation

HRID 247764 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[C:20](=[O:21])[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[C:13]2=[O:22])=[C:4]([F:11])[S:5][C:6]=1[CH2:7][C:8]([OH:10])=[O:9].[CH2:23](O)[CH3:24].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([N:12]2[C:13](=[O:22])[C:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=3[C:20]2=[O:21])=[C:4]([F:11])[S:5][C:6]=1[CH2:7][C:8]([O:10][CH2:23][CH3:24])=[O:9]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 70390576HCID 70390576, compound

Product 1

HCID 70443678HCID 70443678, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(4-chloro-2-fluoro-5-carboxymethylthiophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (1.2 g) and ethanol (1.0 g) in toluene (20 ml), there was added a small amount of p-toluenesulfonic acid, and the mixture was refluxed for 3 hours. Water was added to the reaction mixture. The toluene layer was separated, dried and concentrated. The residue was purified by silica gel chromatography to give 0.1 g of 2-(4-chloro-2-fluoro-5-ethoxycarbonylmethylthiophenyl-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione. nD18 1.5670.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customThe toluene layer was separated
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-74aad69cce514c668a2a611094dde07e
Source dataset
uspto-grants-1987_11
Patent number
US04709049

Reaction notes

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