Ethanol → HCID 14810737, compound

HRID 1647011Notes

Reaction equation

HRID 1647011 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]([CH2:17][C:18]2[S:19][C:20]3[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:21]=3[N:22]=2)[N:7]=1)C.C(O)C.[OH-].[K+]>O1CCCC1>[Cl:27][C:26]1[C:20]2[S:19][C:18]([CH2:17][N:8]3[C:9](=[O:16])[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:6]([CH2:5][C:4]([OH:28])=[O:3])=[N:7]3)=[N:22][C:21]=2[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 15009015HCID 15009015, compound

Product 1

HCID 14810737HCID 14810737, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl-3-(7-chlorobenzothiazol-2-ylmethyl)-4-oxo-3-H-phthalazin-1-ylacetate (800 mg) in a 2:1 mixture of ethanol and tetrahydrofuran (30 ml) was added 5 ml of 1% aqueous potassium hydroxide solution and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated by evaporation under vacuum and the resulting residue was diluted with water (10 ml). Upon adjusting the pH of the solution to around 2 with sufficient 10% HCl, a white precipitate was obtained. The precipitate was collected by filtration, air-dried and then crystallized from methylene chloride (10 ml) to obtain the title compound (yield, 273 mg), m.p. 168° C.

Workup

  1. concentrationThe reaction mixture was concentrated by evaporation under vacuum
  2. additionthe resulting residue was diluted with water (10 ml)
  3. customa white precipitate was obtained
  4. filtrationThe precipitate was collected by filtration
  5. customair-dried
  6. customcrystallized from methylene chloride (10 ml)

Sources & evidence

ORD record
ord-228b7959d5624ec5a4de7b0ce0cedde1
Source dataset
uspto-grants-1993_01
Patent number
US05182391

Reaction notes

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