Hydrochloric Acid → HCID 14934566, compound

HRID 1598581Notes

Reaction equation

HRID 1598581 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH:6]1[CH2:11][C:10](=[O:12])[O:9][C:7]1=[O:8])=[O:4].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClC(Cl)C.C(OCC)(=O)C>[C:7]([CH:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[CH2:11][C:10]([C:17]1[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=1)=[O:12])([OH:9])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7964ChlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 13944508HCID 13944508, compound

Product 1

HCID 14934566HCID 14934566, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 17.58 g of 2-methoxycarbonylaminosuccinic anhydride and 33.77 g of 4-chlorobenzene suspended in 150 ml of dichloroethane was added 33.40 g of anhydrous aluminum chloride under ice cooling, and the mixture was stirred at room temperature for 1 hour. Under ice cooling, to the mixture were added 100 ml of 10% hydrochloric acid and then 500 ml of ethyl acetate. After the organic layer was collected by separation, washed with water and dried, the solvent was removed. The resulting crude crystals were recrystallized from ethyl acetate to obtain 24.2 g of 3-carboxy-3-methoxycarbonylamino-4'-chloropropiophenone.

Workup

  1. customAfter the organic layer was collected by separation
  2. washwashed with water
  3. customdried
  4. customthe solvent was removed
  5. customThe resulting crude crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f5ef9904236e4a7f90c582a3d94d0ad7
Source dataset
uspto-grants-1998_04
Patent number
US05739132

Reaction notes

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