Phenol → HCID 18186854, compound

HRID 1296628Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[N:4][CH:3]=1.[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C(Cl)(Cl)Cl>[O:20]([C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[N:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 165 °C

Procedure

A mixture of the product obtained in example 13, step 2 (1.97 g, 9.92 mmol), phenol (2.43 g, 25.8 mmol), CuO (1.0 g, 12.6 mmol), and K2CO3 (1.43 g, 10.3 mmol) in dioxane (2 mL) was stirred for 4.5 h at 165° C. in a sealed pyrex tube. The reaction mixture was diluted with CHCl3 and filtered through a pad of Celite. The pad was washed with several portions of CHCl3/MeOH (95:5). Solvent removal in vacuo furnished a dark brown oil which was purified by column chromatography on silica gel (14×5 cm) using CHCl3/MeOH (95:5, followed by 90:10) as eluent. The brown oil (1.66 g) was subjected to repeated column chromatography, first on silica gel (18×4 cm) using CHCl3/MeOH (9:1) as eluent and finally on alumina (4×5 cm) using ether/MeOH (95:5) as eluent. This furnished 1.37 g (54%) of the title compound as a light beige oil. HRMS m/z calcd for C14H16N4O (M)30 256.1324, found 256.1321. Anal. (C14H16N4O) C, H, N.

Workup

filtrationfiltered through a pad of Celite
washThe pad was washed with several portions of CHCl3/MeOH (95:5)
customSolvent removal in vacuo
customfurnished a dark brown oil which
customwas purified by column chromatography on silica gel (14×5 cm)

Sources & evidence

ORD record: ord-db2ada8d78e14f8799547893688e05ae
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07247633B2

Reaction notes

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