Hydrochloric Acid → Thiophene-2,5-dicarboxylic acid di-1,3-benzodioxol-5-ylmethyl ester

HRID 583753

Reaction equation

HRID 583753 reaction equation
[C:1](=[O:4])([O-:3])[O-].[Cs+].[Cs+].[S:7]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=[C:8]1[C:15]([OH:17])=[O:16].[CH2:18]1[O:28][C:27]2[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][C:20]=2[O:19]1.ClCCl.Cl>CN(C)C=O.O>[O:3]1[C:27]2[CH:26]=[CH:25][C:22]([CH:23]([O:16][C:15]([C:8]3[S:7][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=3)=[O:17])[C:22]3[CH:25]=[CH:26][C:27]4[O:28][CH2:18][O:19][C:20]=4[CH:21]=3)=[CH:21][C:20]=2[O:4][CH2:1]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 202732,5-Thiophenedicarboxylic acidHCID 887131,3-Benzodioxole, 5-(chloromethyl)-

Product 1

HCID 69693184Thiophene-2,5-dicarboxylic acid di-1,3-benzodioxol-5-ylmethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (4.7 g, 14.4 mmol) was added to a stirred solution of 2,5-thiophenedicarboxylic acid in dimethylformamide (35 mL) under an inert atmosphere at room temperature. After 5 minutes, a solution of 3,4-methylenedioxybenzyl chloride in dichloromethane (3.7 mL, 14.3 mmol) was added. After 24 hours the mixture was stirred into water (150 mL) and acidified with dilute aqueous HCl. After several hours, the precipitate was filtered off, rinsed with water, and dried to afford 0.6 g of thiophene-2,5-dicarboxylic acid di-1,3-benzodioxol-5-ylmethyl ester. Recrystallization of a sample from ethanol gave product with a mp 141-148° C.

Workup

  1. waitAfter several hours
  2. filtrationthe precipitate was filtered off
  3. washrinsed with water
  4. customdried

Sources & evidence

ORD record
ord-e262d475e39c4c9497b1e3db39202161
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Linked notes

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