Ethanol → HCID 14810737, compound

HRID 1461468Notes

Reaction equation

HRID 1461468 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-71198f2f7a27440588f0f2fb837a3960
Source dataset
uspto-grants-1991_12
Patent number
US05075442

Reaction notes

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