Oxalyl chloride → HCID 18977146, compound

HRID 1939910Notes

Reaction equation

HRID 1939910 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([O:14][CH3:15])(=[O:13])[CH2:8][CH2:9][C:10]([OH:12])=O.[C:16]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:18])[CH3:17].[Cl-].[Al+3].[Cl-].[Cl-]>CN(C)C=O.ClC(Cl)C>[C:16]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:10](=[O:12])[CH2:9][CH2:8][C:7]([O:14][CH3:15])=[O:13])=[CH:28][CH:29]=1)(=[O:18])[CH3:17]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 77487monoMethyl succinateHCID 605592HCID 605592, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18977146HCID 18977146, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 63651,1-DichloroethaneSolvent2×

Procedure

45.9 g of oxalyl chloride and 5 drops of dimethylformamide were added to a dichloroethane solution (500 ml) containing 45.5 g of methyl hydrogen succinate, and the mixture was stirred at room temperature for 3 hours. Under ice cooling, a dichloroethane solution (60 ml) containing 31.3 g of [4-(acetylamino)butyl]benzene, and 91.9 g of anhydrous aluminum chloride were added thereto, and the mixture was stirred for 1 hour. The reaction mixture was poured into ice water, and the organic layer was collected by separation. After the organic layer was washed with water and dried, the solvent was removed. The resulting crude crystal was recrystallized from ethyl acetate to obtain 42.3 g of 4-[4-(acetylamino)butyl]-l-(3-methoxycarbonylpropionyl)benzene.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred for 1 hour
  3. customthe organic layer was collected by separation
  4. washAfter the organic layer was washed with water
  5. customdried
  6. customthe solvent was removed
  7. customThe resulting crude crystal was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2f0ad92b1ff6422a884e1a4fd2fac2a5
Source dataset
uspto-grants-1997_12
Patent number
US05698554

Reaction notes

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