Ammonium Chloride → HCID 19041704, compound

HRID 1684006Notes

Reaction equation

HRID 1684006 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH2:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].[Br:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1.[NH4+].[Cl-]>CN(C=O)C>[Br:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[C:6]([CH2:13][C:14]3[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=3[C:16]([O:18][CH3:19])=[O:17])=[C:7]2[CH3:12])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 685274-Bromobenzyl bromideHCID 19041729HCID 19041729, compound

Product 1

HCID 19041704HCID 19041704, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the product of Step 1 (210 mg, 0.68 mmol) in dry DMF (5 mL) at 0° C. was added Nail (30 mg, 0.74 mmol, 60% in oil) followed by 4-bromobenzyl bromide (174 mg, 0.7 mmol). The mixture was stirred at r.t. for 0.5 h. NH4Cl solution was added. The mixture was extracted with EtOAc. Chromatography of the concentrated organic extract gave 272 mg of the title compound.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. extractionChromatography of the concentrated organic extract

Sources & evidence

ORD record
ord-b8c07056d2a947ceaf6dc572bfa18cd8
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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