Toluene → HCID 57021276, compound

HRID 1450174Notes

Reaction equation

HRID 1450174 reaction equation
[CH2:1]([O:3][C:4]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5])[CH3:2].[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:41](=O)[C:40]3[CH2:39][CH2:38][CH2:37][CH2:36][C:35]=3[C:34]2=[O:43])=[CH:29][C:28]=1[CH:44]1[S:48][CH:47]([CH3:49])[CH2:46][S:45]1.[C:50]1(C)C=CC=CC=1>>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:41](=[CH:50][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:40]3[CH2:39][CH2:38][CH2:37][CH2:36][C:35]=3[C:34]2=[O:43])=[CH:29][C:28]=1[CH:44]1[S:48][CH:47]([CH3:49])[CH2:46][S:45]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester2×HCID 15615653HCID 15615653, compound

Product 1

HCID 57021276HCID 57021276, compound

Conditions

Temperature
25 °C

Procedure

1.75 g of (ethoxycarbonylmethylene)triphenylphosphorane were added to a solution of 1.90 g of 2-[4-chloro-3-(4-methyl-1,3-dithiolan-2-yl)phenyl]-4,5,6,7-tetrahydro-2H-isoindol-1,3-dione in 50 ml of toluene. The solution obtained was then refluxed for 5 hours, after which a further 5.25 g of (ethoxycarbonylmethylene)triphenylphosphorane were added in two portions. The reaction mixture was refluxed for a total of 6 hours and then cooled to about 25° C. After separating off solid components and solvent, the residue was treated with diisopropyl ether. The substance crystallizing from diisopropyl ether was separated off and the filtrate was chromatographed on silica gel (eluent: CH2Cl2). Yield : 0.7 g of the title compound as an 85:15 E/Z isomer mixture.

Workup

  1. customThe solution obtained
  2. temperaturewas then refluxed for 5 hours
  3. temperatureThe reaction mixture was refluxed for a total of 6 hours
  4. customAfter separating off solid components and solvent
  5. additionthe residue was treated with diisopropyl ether
  6. customThe substance crystallizing from diisopropyl ether
  7. customwas separated off
  8. customthe filtrate was chromatographed on silica gel (eluent: CH2Cl2)

Sources & evidence

ORD record
ord-76d1c1e67cef4a20bf69e0dc4482e89e
Source dataset
uspto-grants-1997_02
Patent number
US05602074

Reaction notes

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