Water → 2-(4,5-Dichloro-thiophen-2-ylmethyl)-isoindole-1,3-dione

HRID 844011Notes

Reaction equation

HRID 844011 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8]O)[S:5][C:6]=1[Cl:7].[C:10]1(=[O:20])[NH:14][C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.N(C(OCC)=O)=NC(OCC)=O.O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][N:14]2[C:10](=[O:20])[C:11]3[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:13]2=[O:15])[S:5][C:6]=1[Cl:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6809PhthalimideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22612380HCID 22612380, compound

Product 1

HCID 226120382-(4,5-Dichloro-thiophen-2-ylmethyl)-isoindole-1,3-dioneYield 68.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (4,5-Dichloro-thiophen-2-yl)-methanol (0.660 grams, 3.60 mmole), Phthalimide (0.636 grams, 4.32 mmole), and triphenyl phosphene (1.1 grams, 4.32 mmole) in tetrahydrofuran (20 ml) at room temperature was added diethyl azodicarboxylate (0.395 grams, 12.3 mmole) and stirred at room temperature over night. The mixture was poured into 100 ml water and extracted with diethyl ether. The combined extracts were washed with 1 N NaOH, water and brine, dried over MgSO4, filtered, and concentrated to an oil from which triphenylphosphine was crystalized out using diethyl ether/hexane. The mother liquor was concentrated to give a solid which was purified via flash chromatography on silica using 30% ethyl acetate/hexane as eluent to give a yellow solid. This was triturated in hexane to give a white solid (0.772 g). MW 312.18; MS (m/e) 313 (M++1).

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined extracts were washed with 1 N NaOH, water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to an oil from which triphenylphosphine
  6. customwas crystalized out
  7. concentrationThe mother liquor was concentrated
  8. customto give a solid which
  9. customwas purified via flash chromatography on silica using 30% ethyl acetate/hexane as eluent
  10. customto give a yellow solid
  11. customThis was triturated in hexane

Sources & evidence

ORD record
ord-00b6f0555b8c46d3b56778caa0e921b9
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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