N-bromobutanimide → HCID 23156952, compound

HRID 2110112Notes

Reaction equation

HRID 2110112 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:4]=1)#[N:2].C1C(=O)N([Br:21])C(=O)C1>CN(C=O)C.O>[Br:21][C:11]1[O:10][C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 34195404-(2-furyl)benzonitrile

Product 1

HCID 23156952HCID 23156952, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Referring now to Scheme 5 above, to a chilled (ice/water bath) solution of 2-(4-cyanophenyl)furan (28.25 g, 0.167 mol) in DMF (100 ml) was added portionwise NBS (31.20 g, 1.05 eq., freshly recrystallized from nitromethane) with stirring (approximately 1 g portions over course of approximately 40 minutes). The resulting solution was stirred for 2 h at room-temperature, at which point TLC showed consumption of starting material. During the course of the reaction, the color went from yellow to orange and then finally to red. The solution was then diluted with water (approximately 300 ml) to give a pink/red solid, which was collected, washed with water, and air dried. Yield: 39.0 g, 94%. A small sample was recrystallized from MeOH/water to give a pale red crystalline solid, mp 96.5-97° C. 1H NMR (DMSO-d6): 6.80 (d, J=3.6 Hz, 1H), 7.29 (d, J=3.6 Hz, 1H), 7.87 (m, 4H). IR (cm−1): 3142, 3128, 3060, 2226, 1613, 1515, 1475, 1015, 929, 833, 787, 545.

Workup

  1. customfreshly recrystallized from nitromethane)
  2. stirringThe resulting solution was stirred for 2 h at room-temperature, at which point TLC
  3. customconsumption of starting material
  4. customDuring the course of the reaction
  5. customto give a pink/red solid, which
  6. customwas collected
  7. washwashed with water, and air
  8. customdried
  9. customA small sample was recrystallized from MeOH/water
  10. customto give a pale red crystalline solid, mp 96.5-97° C

Sources & evidence

ORD record
ord-5c14cf422afc4aa5a01a5765652234fe
Source dataset
uspto-grants-2009_04
Patent number
US07517893B2

Reaction notes

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