2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-(((4-((4-Chlorophenyl)(thiazol-2-yl)methyl)phenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 1778282Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 4-((4-chlorophenyl)(thiazol-2-yl)methyl)aniline (220 mg, 0.731 mmol, 1 equip) in isopropanol (6 mL) was added 2,2-dimethyl-1,3-dioxane-4,6-dione (140 mg, 0.951 mmol, 1.3 equip) and triethyl orthoformate (443 mg, 2.925 mmol, 4 equip) and the resulting mixture was heated at 100° C. for 3 h. The reaction mixture was cooled to room temperature and concentrated. The residue was purified by MPLC using dichloromethane-methanol as eluent to yield 5-(((4-((4-chlorophenyl)(thiazol-2-yl)methyl)phenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione as a pale yellow foam. 1H NMR (400 MHz, d6-DMSO) δ 11.25 (1H, d), 8.55 (1H, d), 7.82 (1H, d), 7.69 (1H, d), 7.52 (2H, d), 7.38 (2H, d), 7.38-7.30 (4H, m), 6.19 (1H, s), 1.67 (6H, s).

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated
customThe residue was purified by MPLC

Sources & evidence

ORD record: ord-5d4f3335f3b345458b332fe9872e7533
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266835B2

Reaction notes

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