Dimethylformamide → HCID 21073088, compound

HRID 1373255Notes

Reaction equation

HRID 1373255 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[C:12]([O:16][C:17](=[O:29])[NH:18][C:19]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=1)([CH3:21])[CH3:20])([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:12]([O:16][C:17](=[O:29])[NH:18][C:19]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=2[N+:8]([O-:10])=[O:9])[CH:23]=1)([CH3:21])[CH3:20])([CH3:13])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 696914-Chloro-2-fluoro-1-nitrobenzeneHCID 21073089HCID 21073089, compound

Product 1

HCID 21073088HCID 21073088, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-2-fluoronitrobenzene (2.57 g, 14.6 mmols), tert-butyl[1-(3-hydroxyphenyl)-1-methylethyl]carbamate (3.21 g, 12.8 mmols), potassium carbonate (2.02 g, 14.6 mmols) and N,N-dimethylformamide (20 ml) was stirred at 100° C. for 2 hours. The reaction mixture was cooled, then poured into water, and extracted with ethyl acetate. The extract was washed with water and brine, and then dried with anhydrous magnesium sulfate, and the solvent was evaporated away. The residue was purified through silica gel column chromatography to give a crystal of tert-butyl[1-[3-(5-chloro-2-nitrophenoxy)phenyl]-1-methylethyl]carbamate (3.6 g, 69%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customthe solvent was evaporated away
  6. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-cbf93ce553e04ac093bd377bb981d2b4
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

Loading…