Water → HCID 9823426, compound

HRID 1199842Notes

Reaction equation

HRID 1199842 reaction equation
[C:1]([CH2:4][S:5][C:6]1[CH:7]=[C:8]([N:13]2[C:21](=[O:22])[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:14]2=[O:23])[CH:9]=[CH:10][C:11]=1[Cl:12])([OH:3])=[O:2].[CH:24]1(O)[CH2:28][CH2:27][CH2:26][CH2:25]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH:24]1([O:2][C:1]([CH2:4][S:5][C:6]2[CH:7]=[C:8]([N:13]3[C:21](=[O:22])[C:20]4[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=4[C:14]3=[O:23])[CH:9]=[CH:10][C:11]=2[Cl:12])=[O:3])[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 962WaterHCID 7298CyclopentanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 14623470HCID 14623470, compound

Product 1

HCID 9823426HCID 9823426, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(3-Carboxymethylthio-4-chlorophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (3.61 g), cyclopentanol (1.24 g) and p-toluenesulfonic acid monohydrate (0.18 g) were suspended in toluene (10 ml), molecular sieve 3A (0.2 g) was added thereto, and the resultant mixture was heated under reflux for 6 hours. The reaction mixture was allowed to cool, admixed with water and extracted with toluene. The extract was washed with water, dried, and concentrated. The precipitated crystals were washed with methanol to give 1.91 g of 2-(3-cyclopentyloxycarbonylmethylthio-4-chlorophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione. m.p., 57°-59° C.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperatureto cool
  3. extractionextracted with toluene
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated
  7. washThe precipitated crystals were washed with methanol

Sources & evidence

ORD record
ord-f24b8d7eff554bcabcdb361b6eca4495
Source dataset
uspto-grants-1990_02
Patent number
US04902832

Reaction notes

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