6-Bromo-2-(methylthio)benzoxazole → 4-[N-Methyl-N-(6-bromo-2-benzoxazolyl)amino]phenol

HRID 1446879Notes

Reaction equation

C([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH3:12])=[CH:7][CH:6]=1)(=O)C.[Br:13][C:14]1[CH:24]=[CH:23][C:17]2[N:18]=[C:19](SC)[O:20][C:16]=2[CH:15]=1>C(O)(=O)C>[CH3:12][N:11]([C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=1)[C:19]1[O:20][C:16]2[CH:15]=[C:14]([Br:13])[CH:24]=[CH:23][C:17]=2[N:18]=1

Participants

Conditions

Temperature: 180 °C

Procedure

An intimate mixture of 4-(N-methylamino)phenol acetate (7.3 g, 0.04 mole) and 6-bromo-2-(methylthio)benzoxazole (6.0 g, 0.025 mole) was prepared and heated on an oil bath to a temperature of 180° C. The mixture was heated at this temperature for a period of 4 hours during which time acetic acid distilled from the mixture and methyl mercaptan was evolved and was trapped in aqueous sodium hydroxide. The mixture was cooled to form a solid and the solid was extracted with hot toluene (4×100 ml). The toluene solution was filtered hot and the solvent removed by distillation to give a brown solid. The solid was recrystallised from toluene to give the title compound as a grey solid (3.5 g), mp 195° C.

Workup

customwas prepared
distillationdistilled from the mixture and methyl mercaptan
temperatureThe mixture was cooled
customto form a solid
extractionthe solid was extracted with hot toluene (4×100 ml)
filtrationThe toluene solution was filtered hot
customthe solvent removed by distillation
customto give a brown solid
customThe solid was recrystallised from toluene

Sources & evidence

ORD record: ord-2e2ca9a1260e4f188f9a734d27c27aa9
Source dataset: uspto-grants-1982_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04314065

Reaction notes

Loading…