Potassium Carbonate → HCID 19013315, compound

HRID 1729016Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2.56 g (11.2 mmol) of 2-(4'-aminomethylphenyl)nitrobenzene, 2.88 g (12.2 mmol) of 4-chloro-5,6,7,8-tetrahydro-2-trifluoromethylquinazoline, and 8.0 g (58 mmol) of potassium carbonate in DMF was stirred at 100° C. overnight. The reaction mixture was quenched with water and extracted intomethylene chloride/tetrahydrofuran. The organic phase was washed with brine, dried over potassium carbonate, and purified by flash chromatography (elutions of ether/petroleum ether (1:2, then 1:1), then 10% ether/methylene chloride) to give 3.86 g (81%) of 5,6,7,8-tetrahydro-N-[(2'-nitro[1,1'-biphenyl]-4-yl)methyl]-2-(trifluoromethyl)-4-quinazolinamine, mp 150°-151° C.

Workup

customThe reaction mixture was quenched with water
extractionextracted intomethylene chloride/tetrahydrofuran
washThe organic phase was washed with brine
dry with materialdried over potassium carbonate
custompurified by flash chromatography (elutions of ether/petroleum ether (1:2

Sources & evidence

ORD record: ord-61bc329d44a24f6083a1a331ceb2f874
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05330989

Reaction notes

Loading…