N-bromobutanimide → HCID 21460235, compound

HRID 1941227Notes

Reaction equation

HRID 1941227 reaction equation
[N:1]1([C:7]2[O:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:18]N1C(=O)CCC1=O>C(Cl)Cl>[Br:18][C:12]1[C:11](=[O:13])[C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[O:8][C:7]=1[N:1]1[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1312552-(4-Morpholinyl)-4H-1-benzopyran-4-one

Product 1

HCID 21460235HCID 21460235, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-morpholinyl)-4H-benzopyran-4-one (2.0 g, 8.0 mmol) is dissolved in CH2Cl2 (20 mL). N-Bromosuccinimide (1.6 g, 8.2 mmol) is added and the reaction mixture waned slightly and the starting material disappears immediately as evidenced by TLC. The solvent is removed in vacuo and the colorless residue is taken up in EtOAc (200 mL) and washed with water (4×30 mL), brine (50 mL) and dried (MgSO4). Rotary evaporation gives the desired product (2.27 g, 92%) as colorless crystals. mp: 145°-6° c ; IR (mull) 3337, 3016, 2922, 2871, 2855, 1698, 1609, 1585, 1502, 1462, 1378, 1367, 1341, 1303, 1295, 1260, 1234, 996, 812 cm-1 ; 1H NMR (CDCl3, δ) 8.22 (dd, J=7.9, 1.8 Hz, 1H), 7.63 (ddd, J=8.2, 7.4, 1.4 Hz, 1H), 7.44-7.28 (m, 2H), 3.90-3.84 (m, 4H), 3.76-3.69 (m, 4H); LRMS m/e (rel intensity) 311 (55), 309 (55), 253 (14), 231 (17), 230 (100), 172 (21), 121 (20), 120 (15), 110 (61), 41 (16); UV (EtOH) λ max (ε) 216 (18,400), 238 (18,600), 317 (17,040); High resolution MS calc'd. for C13H12 NO3Br: 309.0001. Found: 308.9990. Anal. calc'd. for C13 H12NO3Br: C, 50.34; H, 3.90; N,4.52. Found: C, 50.40; H,4.05; N, 4.46.

Workup

  1. customThe solvent is removed in vacuo
  2. washwashed with water (4×30 mL), brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. customRotary evaporation

Sources & evidence

ORD record
ord-860aed5c497b4e11a0eaee617116acfe
Source dataset
uspto-grants-1997_12
Patent number
US05703075

Reaction notes

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