Phosphorus oxychloride → HCID 136375548, compound

HRID 1757597Notes

Reaction equation

P(Cl)(Cl)([Cl:3])=O.[CH3:6][O:7][C:8]1[C:27]([O:28][CH3:29])=[CH:26][C:11]([CH2:12][CH2:13][NH:14][C:15](=O)[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:10][C:9]=1[OH:30]>C(Cl)(Cl)Cl>[ClH:3].[CH3:29][O:28][C:27]1[CH:26]=[C:11]2[C:10](=[C:9]([OH:30])[C:8]=1[O:7][CH3:6])[C:15]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=[N:14][CH2:13][CH2:12]2

Participants

Conditions

Temperature: 55 °C

Procedure

Phosphoryl chloride (5.42 ml, 58.1 mmol) was added to a chloroform (100 ml)solution of N-(4,5-dimethoxy-3-hydroxyphenethyl)-4-methoxyphenylacetamide (6.71 g, 19.4mmol) at room temperature, and the mixture was stirred under a nitrogen atmosphere at 55° C. for 16 hours. The solvent and excess phosphoryl chloride were removed under reduced pressure, and the resultant residue was recrystallized from methanol-ether to give 6.05 g (yield: 86 %) of the captioned compound as colorless needles. Melting point: 214°-216° C. (dec) High resolution FAB-MS (m/z, (C19H21NO4 +H)+): Calc. 328.1549 Found 328.1526 1H-NMR (300 MHz, CDCl3, δ ppm): 2.85 (2H, t, J=7.4Hz), 3.73 (3H, s), 3.82 (2H, t, J=7.4Hz), 3.91 (3H, s), 3.94 (3H, s), 4.78 (2H,s), 6.38 (1H, s), 6.76 (2H, d, J=8.8Hz), 7.40 (2H, d, J=8.8Hz)

Workup

customThe solvent and excess phosphoryl chloride were removed under reduced pressure
customthe resultant residue was recrystallized from methanol-ether

Sources & evidence

ORD record: ord-35e81446120841068d43aa3db4ac01d9
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05446164

Reaction notes

Loading…