N-bromobutanimide → HCID 10150003, compound

HRID 2086132Notes

Reaction equation

HRID 2086132 reaction equation
C([O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:17]3[C:12](=[C:13]4[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C(=O)C)[C:14]4=[CH:15][CH:16]=3)[O:11][CH2:10][C:9]=2[CH:26]=1)(=O)C.C1C(=O)N([Br:34])C(=O)C1>CN(C=O)C>[Br:34][C:15]1[C:14]2=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=[C:13]2[C:12]2[O:11][CH2:10][C:9]3[CH:26]=[C:5]([OH:4])[CH:6]=[CH:7][C:8]=3[C:17]=2[CH:16]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22728215HCID 22728215, compound

Product 1

HCID 10150003HCID 10150003, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared by reacting 1-(Acetyloxy)-6H-dibenzo[c,h]chromen-8-yl acetate (510 mg, 1.46 mmol), NBS (315 mg, 1.77 mmol), and anhydrous DMF (30 ml) at room temperature for 1.5 hours according to method B. The reaction was concentrated under reduced pressure, dissolved in MeOH (30 ml), and NH3 was bubbled in for 1.5 h while acetate removal was monitored by LC-MS. The reaction was concentrated to a dark sludge and purified by silica chromatography (1:1 EtOAc:hexanes) to afford 340 mg (68%) of product as a tan solid. Mp: decomposes above 130° C.; 1H NMR (500 MHz, DMSO-d6) δ 5.23 (2H, s), 6.72 (1H, d, J=1.9 Hz), 6.81 (1H, dd, J=8.2 Hz, 2.5 Hz), 6.92 (1H, dd, J=7.7 Hz, 1.1 Hz), 7.33 (1H, t, J=8.0 Hz), 7.64 (1H, dd, J=8.5 Hz, 1.1 Hz), 7.68 (1H, d, J=8.5 Hz), 8.01 (1H, s), 9.78 (1H, s), 10.15 (1H, s); MS m/z341/343 (Br pattern) (M−H+).

Workup

  1. customat room temperature
  2. customfor 1.5 hours
  3. concentrationThe reaction was concentrated under reduced pressure
  4. dissolutiondissolved in MeOH (30 ml)
  5. customNH3 was bubbled in for 1.5 h while acetate removal
  6. concentrationThe reaction was concentrated to a dark sludge
  7. custompurified by silica chromatography (1:1 EtOAc:hexanes)

Sources & evidence

ORD record
ord-c56f3ad013424012bd617766a82a8e0b
Source dataset
uspto-grants-2004_04
Patent number
US06723747B2

Reaction notes

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