p-Toluenesulfonic acid → HCID 15023204, compound

HRID 847333Notes

Reaction equation

[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:16]=[CH:15][C:8]2[NH:9][C:10](=[O:14])[CH:11]([CH3:13])[O:12][C:7]=2[CH:6]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:36]1CCOC[CH2:37]1>>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:16]=[CH:15][C:8]2[N:9]([CH2:37][OH:36])[C:10](=[O:14])[CH:11]([CH3:13])[O:12][C:7]=2[CH:6]=1

Participants

Reactant 3

HCID 6101p-Toluenesulfonic acid

HCID 312751,4-Dioxane

HCID 9975627HCID 9975627, compound

Product 1

HCID 15023204HCID 15023204, compoundYield 50%

Conditions

Temperature: 80 °C

Procedure

First, 7-(2-chloro-4-trifluoromethylphenoxy)-2-methyl-2H-1,4-benzoxazine-3 (4H)-one (0.4 g) prepared in Example 1 was dissolved in dioxane (5 ml), p-formaldehyde (0.1 g) and p-toluenesulfonic acid (0.1 g) were added to the solution, and the mixture was stirred at 80° C. for 3 hr. After the completion of the reaction, the reaction mixture was concentrated in vacuo, and the resultant residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=1/1) to prepare the title compound (0.2 g) as a colorless crystal (yield: 50%).

Workup

customAfter the completion of the reaction
concentrationthe reaction mixture was concentrated in vacuo
customthe resultant residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-c418368aa7fa43e6be99891cab27e014
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05141551

Reaction notes

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