Triethylamine → HCID 21190284, compound

HRID 619462Notes

Reaction equation

HRID 619462 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:19](=[O:20])[C:18]3[N:21]4[C:11](=[CH:12][N:13]=[C:14]4[CH:15]=[CH:16][CH:17]=3)[C:10]2=[O:22])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:30][S:31]([Cl:34])(=[O:33])=[O:32]>C(Cl)Cl>[ClH:34].[CH3:30][S:31]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:19](=[O:20])[C:18]3[N:21]4[C:11](=[CH:12][N:13]=[C:14]4[CH:15]=[CH:16][CH:17]=3)[C:10]2=[O:22])=[CH:4][CH:3]=1)(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21190076HCID 21190076, compound

Product 1

HCID 21190284HCID 21190284, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 877 mg (3.0 mmol) of 4-[4-(amino)phenylmethyl]-4,5-dihydro-3H-1,4,8b-triazaacenaphthylene-3,5-dione and 0.63 ml (4.5 mmol) of triethylamine in methylene chloride (60 ml) was added dropwise 0.30 ml (3.9 mmol) of methanesulfonyl chloride while stirring at room temperature. The mixture was stirred for 72 hours at room temperature. The solvent was distilled off. To the residue was added chloroform, washed with 1N-HCl, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: chloroform/methanol=20:1) to afford 274 mg of the desired compound (24.7%, a pale yellow solid).

Workup

  1. stirringThe mixture was stirred for 72 hours at room temperature
  2. distillationThe solvent was distilled off
  3. additionTo the residue was added chloroform
  4. washwashed with 1N-HCl
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by column chromatography (eluent: chloroform/methanol=20:1)

Sources & evidence

ORD record
ord-40300b8d907a4ad482e9edf86eb75aef
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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