4-(Trifluoromethoxy)aniline → HCID 68626825, compound

HRID 1408481Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 4-chloroquinazoline-7-carboxylate (610 mg, 2.75 mmol) in sec-BuOH (5 mL) was added 4-trifluoromethoxyaniline (535.5 mg, 3.02 mmol) at room temperature. The mixture was heated at 100° C. and stirred for 2 h. The solvent was evaporated and the compound was crystallized from CHCl3 and Et2O mixture (3:1). The white crystals were collected by filtration and washed with Et2O. (890 mg, 91% Yield). MS m/z 364.10 (M+1).

Workup

customThe solvent was evaporated
customthe compound was crystallized from CHCl3 and Et2O mixture (3:1)
filtrationThe white crystals were collected by filtration
washwashed with Et2O

Sources & evidence

ORD record: ord-1f2a37b24b834064aa176ef473e52b7b
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921336B2

Reaction notes

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