Hydrochloric Acid → HCID 14810636, compound

HRID 2165065Notes

Reaction equation

HRID 2165065 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:4][NH:3]1.[H-].[Na+].[Br:20][C:21]1[CH:22]=[CH:23][C:24]2[S:28][C:27]([CH2:29]Br)=[N:26][C:25]=2[CH:31]=1.Cl>CN(C)C=O>[Br:20][C:21]1[CH:22]=[CH:23][C:24]2[S:28][C:27]([CH2:29][N:3]3[C:2](=[O:1])[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:4]3)=[N:26][C:25]=2[CH:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 348622Ethyl 2-(4-oxo-3,4-dihydrophthalazin-1-yl)acetateHCID 144586425-Bromo-2-(bromomethyl)-1,3-benzothiazole

Product 1

HCID 14810636HCID 14810636, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 4-oxo-3H-phthalazin-1-ylacetate (11.6 g.) and sodium hydride (288 g; 50% w/w dispersion in mineral oil) in dimethylformamide (150 ml) was added 5-bromo-2-bromomethylbenzothiazole (16.8 g) and the resulting mixture stirred at room temperature for 1 hour. This reaction mixture was poured over ice-water (500 ml.); sufficient 10% HCl was added to adjust the pH to about 4.0 and the precipitated crude solid was collected. This was chromatographed over silica gel to obtain the product (yield: 5.6 g; m.p. 160°-161° C.).

Workup

  1. customthe precipitated crude solid
  2. customwas collected
  3. customThis was chromatographed over silica gel
  4. customto obtain the product (yield: 5.6 g; m.p. 160°-161° C.)

Sources & evidence

ORD record
ord-dbaf9874a1cb420a9c81e011b3f9ed10
Source dataset
uspto-grants-1990_07
Patent number
US04939140

Reaction notes

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