Benzoyl chloride → 3-Benzamido-4-(2,4-bis(1,1-dimethylpropyl)phenoxy)-pyridine

HRID 1656558Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:19])([CH3:18])[CH2:16][CH3:17])=[CH:11][C:10]=1[C:20]([CH3:24])([CH3:23])[CH2:21][CH3:22].[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>O1CCCC1>[C:25]([NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:19])[CH2:16][CH3:17])=[CH:11][C:10]=1[C:20]([CH3:23])([CH3:24])[CH2:21][CH3:22])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 10 °C

Procedure

3-Amino-4-(2,4-bis(1,1-dimethylpropyl)phenoxy)-pyridine (3.0 g, 9.2 mmol) was dissolved in tetrahydrofuran (10 mL) and cooled to 10° C. Benzoyl chloride (1.3 g, 9.2 mmol) in tetrahydrofuran (10 mL) was added dropwise. Triethylamine (0.93 g, 9.2 mmol) in tetrahydrofuran (5 mL) was added and the mixture warmed to room temperature and stirred for 2 hours. The mixture was submitted to standard aqueous acidic workup. The crude solid obtained was recrystallized from acetonitrile to yield the title product as a white solid in 80% yield, m.p. 253° C. Mass spectral and NMR data were consistent with the proposed structure.

Workup

temperaturethe mixture warmed to room temperature
customThe crude solid obtained
customwas recrystallized from acetonitrile

Sources & evidence

ORD record: ord-dd1d40fe579d46e0a4f8c9da99991f95
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05254592

Reaction notes

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