Dichloromethane → HCID 178474118, compound

HRID 2424324Notes

Reaction equation

HRID 2424324 reaction equation
C(O[C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[N:18]=[N:19][C:20]([Cl:32])=[CH:21][C:22]=2[O:23]C(=O)C2C=CC=CC=2)=[C:12](C)[CH:11]=1)(=O)C1C=CC=CC=1.ClCCl.[CH2:37]([N:39](CC)CC)[CH3:38].C(Cl)(=[O:46])C>[Cl-].[Na+].O>[Cl:32][C:20]1[N:19]=[N:18][C:17]([O:16][C:13]2[CH:14]=[CH:15][CH:10]=[CH:11][C:12]=2[NH:39][C:37](=[O:46])[CH3:38])=[C:22]([OH:23])[CH:21]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57486495HCID 57486495, compound

Product 1

HCID 178474118HCID 178474118, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

18.0 mg (0.0756 mmol) of 3-(2-aminophenoxy)-3-chloro-4-pyridazinol obtained in Example 641 was mixed with dichloromethane (0.8 mL), 0.050 mL (0.36 mmol) of triethyl-amine, then 0.010 mL (0.14 mmol) of acetyl chloride were added to the mixture in an ice bath with stirring, and the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into brine, and extracted with tetrahydrofuran. The organic layers were combined, washed with brine and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by preparative thin-layer chromatography (available from MERCK CO., 1.05715, developed by dichloromethane:methanol=10:1) to obtain 3.6 mg (0.0129 mmol, Yield: 17.1%) of N-{2-[(6-chloro-4-hydroxy-3-pyridazinyl)oxy]phenyl}acetamide (Compound No. 380).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 hours
  2. extractionextracted with tetrahydrofuran
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by preparative thin-layer chromatography (available from MERCK CO., 1.05715, developed by dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-21e4a7d0cd72459ab1daa52f32bdcaa5
Source dataset
uspto-grants-2011_06
Patent number
US07964531B2

Reaction notes

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