Succinic anhydride → HCID 18929767, compound

HRID 1598576Notes

Reaction equation

HRID 1598576 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][CH:12]1[CH2:20][CH2:19][C:15]2[S:16][CH:17]=[CH:18][C:14]=2[CH2:13]1)(=[O:10])=[O:9].[C:21]1(=[O:27])[O:26][C:24](=[O:25])[CH2:23][CH2:22]1.[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[C:24]([CH2:23][CH2:22][C:21]([C:17]1[S:16][C:15]2[CH2:19][CH2:20][CH:12]([NH:11][S:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])(=[O:9])=[O:10])[CH2:13][C:14]=2[CH:18]=1)=[O:27])([OH:26])=[O:25]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 6451240Aluminum(III) ChlorideHCID 18929784HCID 18929784, compound

Product 1

HCID 18929767HCID 18929767, compoundYield 116.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To 2.25 g of 5-[(2-methylphenyl)sulfonylamino]-4,5,6,7-tetrahydrobenzo[b]thiophene and 1.61 g of succinic anhydride suspended in 25 ml of dichloroethane was added 4.39 g of anhydrous aluminum chloride under ice cooling, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. After the resulting organic layer was washed and dried, the solvent was removed to obtain 3.47 g of 2-(3-carboxypropionyl)-5-[(2-methylphenyl)sulfonylamino]-4,5,6,7-tetrahydrobenzo[b]thiophene.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the resulting organic layer was washed
  3. customdried
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-da7e363081054e35a1035af2b6c53ccb
Source dataset
uspto-grants-1998_04
Patent number
US05739132

Reaction notes

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