Hydrochloric Acid → HCID 70594922, compound

HRID 1732283Notes

Reaction equation

HRID 1732283 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[CH2:6][CH:7]([C:9]([O:11]CC)=[O:10])[O:8][C:4]=2[C:3]=1[Cl:16].[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[S:22](Cl)(=[O:24])=[O:23].[Cl-].[Al+3].[Cl-].[Cl-].Cl>>[OH2:8].[Cl:1][C:2]1[C:15]([S:22]([C:18]2[S:17][CH:21]=[CH:20][CH:19]=2)(=[O:24])=[O:23])=[CH:14][C:5]2[CH2:6][CH:7]([C:9]([OH:11])=[O:10])[O:8][C:4]=2[C:3]=1[Cl:16].[Cl:1][C:2]1[C:15]([S:22]([C:18]2[S:17][CH:21]=[CH:20][CH:19]=2)(=[O:24])=[O:23])=[CH:14][C:5]2[CH2:6][CH:7]([C:9]([OH:11])=[O:10])[O:8][C:4]=2[C:3]=1[Cl:16]

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 855182-Thiophenesulfonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12747889Ethyl 6,7-dichloro-2,3-dihydro-1-benzofuran-2-carboxylate

Product 1

HCID 70594922HCID 70594922, compound

Conditions

Temperature
80 °C

Procedure

To a well stirred mixture of ethyl 6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylate (5.2 g) and 2-thienylsulfonyl chloride (3.6 g) protected from the atmosphere with a calcium chloride tube is added the anhydrous aluminum chloride (2.6 g) over a five minute period. The reaction mixture is stirred at 25° C. for 18 hours and at 90° C. for one hour, then poured into ice water (150 ml) and hydrochloric acid (15 ml). The esterified product is extracted into ether, washed with brine, dried over magnesium sulfate and the ether distilled at reduced pressure. The residue is warmed (80° C.) in 10% NaOH (100 ml) for one hour to obtain a solution which is acidified with hydrochloric acid (25 ml) to obtain the product as a viscous oil. The product is extracted into ether, washed with brine, dried over magnesium sulfate and the ether distilled at reduced pressure. The 6,7-dichloro-2,3-dihydro-5-(2-thienylsulfonylbenzofuran-2-carboxylic acid hemihydrate melts at 189°-193° C. after purification by column chromatography.

Workup

  1. customprotected from the atmosphere with a calcium chloride tube
  2. stirringThe reaction mixture is stirred at 25° C. for 18 hours and at 90° C. for one hour
  3. extractionThe esterified product is extracted into ether
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. distillationthe ether distilled at reduced pressure
  7. customto obtain a solution which

Sources & evidence

ORD record
ord-d2805bda37b94e7983648d1230778de4
Source dataset
uspto-grants-1980_12
Patent number
US04237130

Reaction notes

Loading…