N-bromobutanimide → HCID 21029604, compound

HRID 1922421Notes

Reaction equation

HRID 1922421 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.C1C(=O)N([Br:24])C(=O)C1>CN(C=O)C.O>[Br:24][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([CH:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)[CH2:9][CH2:10]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 20594145HCID 20594145, compound

Product 1

HCID 21029604HCID 21029604, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of compound 2 (1.12 g, 5.176 mmol) in dry DMF (10 mL) was treated with NBS (0.92 g, 5.176 mmol) in dry DMF (5 mL) at 0° C. over a period of 5 min. and stirring was continued at same temperature for 3 h. The reaction was diluted with water (100 mL) and product was extracted into ethyl acetate (2×25 mL). The combined ethyl acetate layer was washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated and crude material was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 3:97) to obtain compound 3 (1.15 g, 76%) as a syrup. 1H NMR (DMSO-d6) δ 7.14-7.06 (m, 2H), 6.37 (d, 1H, J=8.4 Hz), 3.35-3.24 (m, 3H, merged with water peak), 2.93-2.80 (m, 4H), 2.16 (s, 3H), 2.00-1.88 (m, 2H), 1.64-1.55 (m, 4H); EI-MS (m/z, %): 293, 295 (M+, bromine isotope, 47), 98 (59), 97 (100), 71 (47).

Workup

  1. extractionwas extracted into ethyl acetate (2×25 mL)
  2. washThe combined ethyl acetate layer was washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was evaporated
  5. customcrude material was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 3:97)

Sources & evidence

ORD record
ord-466b697ede0641ab8adad2cbe4cf229f
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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