Benzoyl chloride → HCID 57581555, compound

HRID 1689965Notes

Reaction equation

HRID 1689965 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][NH:15][CH:14]([C:18]([O:20][CH3:21])=[O:19])[CH2:13]2)=[N:4][N:3]=1.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>[C:22]([N:15]1[CH2:16][CH2:17][N:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([Cl:1])=[N:3][N:4]=2)[CH2:13][CH:14]1[C:18]([O:20][CH3:21])=[O:19])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 2

HCID 7412Benzoyl chlorideHCID 57581498HCID 57581498, compound

Product 1

HCID 57581555HCID 57581555, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Procedure

Methyl 4-(4-chlorophthalazin-1-yl)piperazine-2-carboxylate (563 mg, 1.84 mmol) was dissolved in DMF (6 mL) and N,N-diisopropylethylamine (1 mL). Benzoyl chloride (0.23 mL, 2.02 mmol) was added and the mixture stirred at rt for 16 hours. The reaction was taken up in ethyl acetate (80 mL), washed with aqueous K2CO3 (10%), water, and then saturated sodium chloride. The organics were dried (MgSO4) and evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/0-75% ethyl acetate gave an off-white foam. MS (M+H)+=381.8.

Workup

  1. washwashed with aqueous K2CO3 (10%), water
  2. dry with materialThe organics were dried (MgSO4)
  3. customevaporated
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-dbd35a960ef94488b508e0194f50315e
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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