Potassium Carbonate → HCID 57961759, compound

HRID 541873Notes

Reaction equation

HRID 541873 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[NH2:12][C:13]1[CH:14]=[C:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:9]([C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][NH:12][C:13]1[CH:14]=[C:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH:16]=[CH:17][CH:18]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 12877220tert-butyl N-(3-aminophenyl)carbamate

Product 1

HCID 57961759HCID 57961759, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(bromomethyl)-3-nitro-benzene (4.50 g, 0.021 mol) and tert-butyl (3-aminophenyl)carbamate (4.34 g, 0.021 mol) in N,N-dimethylformamide (50 mL) was added potassium carbonate (4.32 g, 0.03 mol). The resultant mixture was stirred at room temperature overnight and the reaction was complete. The reaction mixture was filtered first to remove K2CO3, and then quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with water and then dried (Na2SO4), filtered and concentrated to give the desired product as a light brown gel (6.94 g, 97%). LCMS for C18H22N3O4 (M+H)+: m/z=344.1.

Workup

  1. filtrationThe reaction mixture was filtered first
  2. customto remove K2CO3
  3. customquenched with water
  4. additionEtOAc was added
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with EtOAc twice
  7. washThe combined organic layers were washed with water
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f116cc8d1b26416a8b7cd7804bf61061
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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