Acetyl chloride → HCID 178474863, compound

HRID 24946Notes

Reaction equation

HRID 24946 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16]/[C:17](=[C:24]3\[C:25](=[O:36])[NH:26][C:27]4[C:32]\3=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=4)/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.[C:37](Cl)(=[O:39])[CH3:38]>ClCCl>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]([C:10]2[CH:11]=[CH:12][C:13]([NH:16]/[C:17](=[C:24]3\[C:25](=[O:36])[NH:26][C:27]4[C:32]\3=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=4)/[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:14][CH:15]=2)[C:37](=[O:39])[CH3:38])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 178517279HCID 178517279, compound

Product 1

HCID 178474863HCID 178474863, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

486 mg (1.0 mmol) of (Z)-3-{1-[4-(2-morpholinoethylamino)-phenylamino]-1-phenyl-methylidene}-5-nitro-2-indolinone (Example 332) are dissolved in 30 ml of dichloromethane and combined with 1.2 ml (16 mmol) of acetylchloride. The mixture is stirred for 1 hour at ambient temperature. The precipitate is removed by suction filtering and the reaction solution is washed with water. Then the solvent is eliminated in vacuo, the residue is dissolved in 20 ml of methanol and combined with 4 ml of 1 N sodium hydroxide solution. The mixture is stirred for 30 minutes at ambient temperature and then the solvent is eliminated in vacuo. The residue is suspended in water and a little ether. Then the product is suction filtered and dried.

Workup

  1. customThe precipitate is removed by suction
  2. filtrationfiltering
  3. washthe reaction solution is washed with water
  4. dissolutionthe residue is dissolved in 20 ml of methanol
  5. stirringThe mixture is stirred for 30 minutes at ambient temperature
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-ac56b62405a5402d82972ca174561d33
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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