Dimethylformamide → HCID 21073110, compound

HRID 1373214Notes

Reaction equation

HRID 1373214 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[NH2:23])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:29]Cl.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[NH:23][CH2:29][C:28]2[CH:31]=[CH:32][C:33]([Cl:34])=[C:26]([Cl:25])[CH:27]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 76093,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 21072922HCID 21072922, compound

Product 1

HCID 21073110HCID 21073110, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of tert-butyl[3-(2-amino-5-chlorophenoxy)benzyl]carbamate (3.49 g, 10 mmols), 3,4-dichlorobenzyl chloride (2.1 ml, 15 mmols), potassium carbonate (1.38 g. 10 mmols) and N,N-dimethylformamide (30 ml) was stirred at room temperature for 12 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The extract was washed with brine, then dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography to give an oil of tert-butyl[3-[5-chloro-2-(3,4-dichlorobenzylamino)phenoxy]benzyl]carbamate (3.03 g, 59.8%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-5581d3e1d5b84a0893e4ce46c48e5843
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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