Hydrochloric Acid → 6,7-Dichloro-5-((dimethylamino)sulfonyl)-2,3-dihydro-2-benzofurancarboxylic acid

HRID 542748Notes

Reaction equation

HRID 542748 reaction equation
[CH3:1][N:2]([CH3:22])[S:3]([C:6]1[C:7]([Cl:21])=[C:8]([Cl:20])[C:9]2[O:13][CH:12]([C:14]([O:16]CC)=[O:15])[CH2:11][C:10]=2[CH:19]=1)(=[O:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl>O1CCCC1>[CH3:1][N:2]([CH3:22])[S:3]([C:6]1[C:7]([Cl:21])=[C:8]([Cl:20])[C:9]2[O:13][CH:12]([C:14]([OH:16])=[O:15])[CH2:11][C:10]=2[CH:19]=1)(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 13688871HCID 13688871, compound

Product 1

HCID 598026,7-Dichloro-5-((dimethylamino)sulfonyl)-2,3-dihydro-2-benzofurancarboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1 g of ethyl 5-(N,N-dimethylsulfamoyl)-6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylate (Ia-1) dissolved in 9 ml of tetrahydrofuran is added 14 ml of 15% aqueous potassium carbonate and the mixture stirred for 72 hours at room temperature. The reaction mixture is condensed under reduced pressure to leave residue, which is made acid (pH 5.0) with 10% hydrochloric acid and extracted with ethyl acetate. The organic layer is dried and evaporated under reduced pressure to leave an oil, which is then recrystallized from either to give 0.868 g of 5-(N,N-dimethylsulfamoyl)-6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic acid (I b-28), yielded in 94%, m.p. 154° C.

Workup

  1. customcondensed under reduced pressure
  2. customto leave residue, which
  3. extractionextracted with ethyl acetate
  4. customThe organic layer is dried
  5. customevaporated under reduced pressure
  6. customto leave an oil, which
  7. customis then recrystallized from either

Sources & evidence

ORD record
ord-350084a6aa4841f3a79054211653a824
Source dataset
uspto-grants-1987_04
Patent number
US04659709

Reaction notes

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