Water → HCID 178519521, compound

HRID 2305768Notes

Reaction equation

HRID 2305768 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[Cl:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9].[OH:15][C:16]1[CH:20]=[C:19]([N:21]2[C:25](=[O:26])[C:24]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])[N:18]([C:32]2[C:37]([Cl:38])=[CH:36][C:35]([Cl:39])=[CH:34][C:33]=2[Cl:40])[N:17]=1.O>ClC(Cl)C(Cl)Cl.CO>[Cl:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([C:20]1[C:16]([OH:15])=[N:17][N:18]([C:32]2[C:33]([Cl:40])=[CH:34][C:35]([Cl:39])=[CH:36][C:37]=2[Cl:38])[C:19]=1[N:21]1[C:22](=[O:31])[C:23]2=[CH:30][CH:29]=[CH:28][CH:27]=[C:24]2[C:25]1=[O:26])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 691102-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 178514960HCID 178514960, compound

Product 1

HCID 178519521HCID 178519521, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 65911,1,2,2-TetrachloroethaneSolvent

Procedure

Aluminum trichloride (2.34 g, 17.6 mmol) was added to a solution of 2-chlorobenzoyl chloride in 60 mL of 1,1,2,2-tetrachloroethane and the resulting mixture was stirred for 30 minutes at room temperature. Then 2.87 g of the compound of Step B was added all at once and the reaction mixture was refluxed overnight. The cooled mixture was poured into water and the aqueous phase was extracted three times with ethyl acetate. The organic extracts were dried with brine and magnesium sulfate and evaporated to give a red oil which was taken up in methanol and crystallized to give the title compound, 2.97 g (77%), m.p. 245 -246° C.

Workup

  1. temperaturewas refluxed overnight
  2. extractionthe aqueous phase was extracted three times with ethyl acetate
  3. dry with materialThe organic extracts were dried with brine and magnesium sulfate
  4. customevaporated
  5. customto give a red oil which
  6. customcrystallized

Sources & evidence

ORD record
ord-d0e8db3a9e274ba488e00b2290f8c962
Source dataset
uspto-grants-2002_08
Patent number
US06441018B2

Reaction notes

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