HCID 19808814, compound → HCID 19808762, compound

HRID 374020Notes

Reaction equation

HRID 374020 reaction equation
C1([N:7]2[C:23](=[O:24])[C:22]3[C:21]4[C:20]5[C:15](=[CH:16][C:17]([Br:27])=[C:18]([O:25][CH3:26])[CH:19]=5)[N:14]([CH2:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:13]=4[C:12]([CH2:35]Br)=[CH:11][C:10]=3[C:8]2=[O:9])C=CC=CC=1.[CH3:37][NH:38][CH3:39].[CH:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[C:40]1([N:7]2[C:23](=[O:24])[C:22]3[C:21]4[C:20]5[C:15](=[CH:16][C:17]([Br:27])=[C:18]([O:25][CH3:26])[CH:19]=5)[N:14]([CH2:28][C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)[C:13]=4[C:12]([CH2:35][N:38]([CH3:39])[CH3:37])=[CH:11][C:10]=3[C:8]2=[O:9])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

4

Reactant 2

HCID 19808814HCID 19808814, compoundHCID 22381569HCID 22381569, compound

Product 1

HCID 19808762HCID 19808762, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

450 mg of N-phenyl-9-benzyl-7-bromo-1-bromomethyl-6-methoxycarbazole-3,4-dicarboximide was dissolved in 5 ml of methylene chloride. Thereto was added 0.5 ml of 20% dimethylamine-benzene solution. The resulting mixture was stirred for 1 hour at room temperature. To the reaction mixture was added 10 ml of methylene chloride. The resulting mixture was washed with an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from n-propanol to obtain 370 mg (yield: 87%) of N-phenyl-9-benzyl-7-bromo-1-dimethylaminomethyl-6-methoxycarbazole-3,4-dicarboximide as yellow crystals.

Workup

  1. washThe resulting mixture was washed with an aqueous saturated sodium hydrogencarbonate solution
  2. dry with materialan aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation under reduced pressure
  4. customThe residue was recrystallized from n-propanol

Sources & evidence

ORD record
ord-589f9efa21a84bf8bd119f162eed76c0
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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