2-(4-Morpholinyl)-4H-1-benzopyran-4-one → HCID 21460174, compound

HRID 1941226Notes

Reaction equation

HRID 1941226 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.[Cl:18]OC(C)(C)C>C(Cl)Cl>[Cl: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 1312552-(4-Morpholinyl)-4H-1-benzopyran-4-oneHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 21460174HCID 21460174, compoundYield 91%

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). t-Butyl hypochlorite (1.0 mL, 8.5 mmol) is added dropwise at 23° C. The reaction mixture is warmed slightly and is finished almost instantaneously. The solvent is removed in vacuo and the residue is taken up in EtOAc (200 mL). The organic layer is washed with water (2×50 mL) and brine (80 mL), then dried (MgSO4). The solution is concentrated in vacuo giving colorless crystals which are recrystallized from EtOAc to give the desired product (1.86 g, 91%) Mp 127°-8° C.; IR (mull) 2962, 2923, 2856, 1635, 1612, 1597, 1562, 1555, 1466, 1457, 1325, 1233, 1119, 872, 762 cm-1 ; 1H NMR (200 Mhz, CDCl3, δ) 8.20 (br d, J=7.5 Hz, 1H), 7.60 (ddd, J=9.1, 6.7, 1.7 Hz, 1H), 7.36 (m, 2 H), 3.88 (m, 4H), 3.74 (m, 4H); MS m/e (rel intensity) 267 (33), 266 (15), 265 (100), 231 (15), 230 (98), 209 (16), 207 (45), 120 (27), 110 (19), 41 (16); UV (EtOH) λ max (ε) 214 (18,900), 238 (18,160), 300 sh (11,530); Anal. calc'd. for C13H12NO3Cl: C, 58.76; H, 4.55; N, 5.27. Found: C, 58.82; H, 4.58; N, 5.37.

Workup

  1. temperatureThe reaction mixture is warmed slightly
  2. customThe solvent is removed in vacuo
  3. washThe organic layer is washed with water (2×50 mL) and brine (80 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationThe solution is concentrated in vacuo
  6. customgiving colorless crystals which
  7. customare recrystallized from EtOAc

Sources & evidence

ORD record
ord-e3d60be2987c4a8aba69b20a2dc0003c
Source dataset
uspto-grants-1997_12
Patent number
US05703075

Reaction notes

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