Benzoyl chloride → HCID 178509345, compound

HRID 49912

Reaction equation

HRID 49912 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:22]=[CH:21][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[N:13][N:12]=2)=[CH:8][CH:7]=1.C[Si]([C:27]#[N:28])(C)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl.O>[C:29]([N:13]1[N:12]=[C:11]([NH:10][C:9]2[CH:8]=[CH:7][C:6]([Cl:5])=[CH:22][CH:21]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]1[C:27]#[N:28])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 82115Trimethylsilyl cyanideHCID 6451240Aluminum(III) ChlorideHCID 227419971-(4-Chloroanilino)phthalazine

Product 1

HCID 178509345HCID 178509345, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Under N2 atmosphere, first 164 mg (1.2 mmol) anhydrous aluminium chloride is added to 12.6 g (49.3 mmol) 1-(4-chloroanilino)phthalazine in 90 ml dichloromethane, followed by 12.3 ml (98.6 mmol) trimethylsilyl cyanide. Finally, 11.5 ml (98.6 mmol) benzoyl chloride is added under ice cooling and stirred for 3 h at RT. The suspension is poured onto 0.6 ml water, filtered off, washed with water, and dried. Mixing in 150 ml boiling ethanol yields pure title compound: m.p.: 201-202° C.; Anal. calc.(C22H15N4ClO) C, 68.31%; H, 3.91%; N, 14.48%, Cl, 9.16%. found C, 68.03%; H, 3.89%; N, 14.22%, Cl, 9.42%.

Workup

  1. filtrationfiltered off
  2. washwashed with water
  3. customdried
  4. additionMixing in 150 ml

Sources & evidence

ORD record
ord-4f563b29aff94c62bab9fc1f48d41eee
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Linked notes

Loading…