2-Bromoaniline → HCID 23111116, compound

HRID 1920502Notes

Reaction equation

HRID 1920502 reaction equation
Cl.C(N=C=NCCCN(C)C)C.ON1C2N=CC=CC=2N=N1.[Br:23][C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH2:26].[CH2:31]([N:33]([CH2:41][CH2:42][CH2:43][C:44](O)=[O:45])[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[CH:35]=1)[CH3:32]>C(OCC)(=O)C.C(N(CC)CC)C.ClCCl>[Br:23][C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH:26][C:44](=[O:45])[CH2:43][CH2:42][CH2:41][N:33]([CH2:31][CH3:32])[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[CH:35]=1

Participants

8

Reactant 4

HCID 119922-BromoanilineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23111119HCID 23111119, compound

Product 1

HCID 23111116HCID 23111116, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (150 mg), 1-hydroxy-7-azabenzotriazole (106 mg), dichloromethane (2 ml), 2-bromoaniline (134 μl), and triethylamine (162 μl) were added to the compound (100 mg) obtained in Step 2, and the mixture was stirred at room temperature for 17 hours. The reaction mixture was diluted with ethyl acetate, washed with water, and dried over magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel chromatography (hexane-ethyl acetate) to give the title compound (56 mg).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5ca28fe9d82246098c9856e399f56556
Source dataset
uspto-grants-2012_05
Patent number
US08168827B2

Reaction notes

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