N-bromobutanimide → HCID 49766558, compound

HRID 2077261Notes

Reaction equation

HRID 2077261 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C1C(=O)N([Br:19])C(=O)C1.C(OCC)(=O)C.CCCCCC>CC#N>[NH2:1][C:2]1[C:7]([Br:19])=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 49847212-Amino-5-NitrophenolHCID 21226206Ethyl acetate hexane

Product 1

HCID 49766558HCID 49766558, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-amino-5-nitrophenol (97, 24 g, 156 mmol) in CH3CN (1 L) was treated with NBS (28.8 g, 160.8 mmol) at room temperature. After stirring for 1 hour, the solvent was removed to afford brown precipitate, which was taken up with ethyl acetate:hexane (1:1). The precipitate was filtered and was used for the next step without further purification (33 g, 91%). A small amount of sample was purified by column chromatography on silica gel for analysis; 1H NMR (500 MHz, CD3OD): δ 4.93 (brs, 3H), 7.50 (d, 1H, J=2.4 Hz), 7.89 (d, 1H, J=2.4 Hz); 13C NMR (125 MHz, CD3OD): δ 105.5, 108.7, 121.8, 138.5, 143.7, 144.8; HRMS (FAB) calcd for C6H5BrN2O3 (M+) 231.9484, found 231.9479.

Workup

  1. customthe solvent was removed
  2. customto afford brown precipitate, which
  3. filtrationThe precipitate was filtered
  4. customwas used for the next step without further purification (33 g, 91%)
  5. customA small amount of sample was purified by column chromatography on silica gel for analysis

Sources & evidence

ORD record
ord-4fdb0d4926374af39cee287a6e8644df
Source dataset
uspto-grants-2011_04
Patent number
US07928127B2

Reaction notes

Loading…