4-Nitrophenol → HCID 86665995, compound

HRID 1522325Notes

Reaction equation

HRID 1522325 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]([C:23]1[NH:24][CH:25]=[CH:26][N:27]=1)=[O:22])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C(Cl)(=O)C(Cl)=O.[N+:34]([C:37]1[CH:42]=CC(O)=[CH:39][CH:38]=1)([O-:36])=[O:35].CCN(CC)CC>C(Cl)Cl>[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]([C:23]1[NH:27][CH:26]=[CH:25][N:24]=1)=[O:22])([O:6][C:7]1[CH:39]=[CH:38][C:37]([N+:34]([O-:36])=[O:35])=[CH:42][CH:8]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86665996HCID 86665996, compound

Product 1

HCID 86665995HCID 86665995, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 16 (1.2 g, 3.0 mmol) dissolved in 25 mL of CH2Cl2 was added oxalyl chloride (0.65 n-flL, 7.5 mmol) dropwise at 0° C. The reaction mixture was allowed to slowly warm to room temperature. After stirring for 8 h, the mixture was concentrated to remove excess oxalyl chloride. The crude residue was redissolved in 20 mL of CH2Cl2, followed by the addition of 4-nitrophenol (414 mg, 3.0 mmol) and Et3N (0.80 mL, 6.0 mmol). After stirring at room temperature for 10 h, the reaction mixture was concentrated. The residue was purified by flash chromatography (hexane/EA=1:1) to give 601 mg (41%) of pure 17. 1H NMR (CDCl3, 500 MHz) δ 8.16 (d, J=9.0 Hz, 2H), 8.10 (s, 1H), 7.37 (s, 1H), 7.32 (d, J=9.0 Hz, 2H), 7.01 (s, 1H), 4.35 (t, J=6.5 Hz, 2H), 4.11 (m, 2H), 1.87 (m, 2H), 1.72 (m, 2H), 1.62 (m, 2H), 1.38-1.17 (br m, 20H). 31P NMR (CDCl3, 500 MHz) δ 30.49.

Workup

  1. concentrationthe mixture was concentrated
  2. customto remove excess oxalyl chloride
  3. dissolutionThe crude residue was redissolved in 20 mL of CH2Cl2
  4. stirringAfter stirring at room temperature for 10 h
  5. concentrationthe reaction mixture was concentrated
  6. customThe residue was purified by flash chromatography (hexane/EA=1:1)
  7. customto give 601 mg (41%) of pure 17

Sources & evidence

ORD record
ord-29aed8562b4642eda21a23c4505d9857
Source dataset
uspto-grants-2015_07
Patent number
US09074300B2

Reaction notes

Loading…