Dimethylformamide → HCID 20554735, compound

HRID 1105744Notes

Reaction equation

[CH3:1][N:2]([C:14]1[CH:26]=[CH:25][C:17]([O:18]C(C)C(OC)=O)=[CH:16][CH:15]=1)[C:3]1[N:4]=[N:5][C:6]2[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:7]=2[N:8]=1.Br[C:28]([CH3:35])([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>ClCCl>[CH3:1][N:2]([C:14]1[CH:26]=[CH:25][C:17]([O:18][C:28]([CH3:35])([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:16][CH:15]=1)[C:3]1[N:4]=[N:5][C:6]2[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:7]=2[N:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-[N-methyl-N-(7-chloro-1,2,4-benzotriazin-3-yl)amino]phenol (1.5 g; Example 6 part (a)), ethyl 2-bromo-2-methylpropionate (1.23 g), anhydrous potassium carbonate (0.87 g) and dimethylformamide (15 ml) was heated, with stirring, at a temperature of 100° C. for a period of 3 days. The cooled solution was poured into dichloromethane and the mixture was washed with water. The aqueous phase was dried (over anhydrous magnesium sulfate) and the solvent was removed by distillation under reduced pressure to give an oil. The crude product was purified by chromatography over silica gel (eluent dichloromethane) to give the title compound (0.9 g) as a red oil.

Workup

temperaturewas heated
washthe mixture was washed with water
dry with materialThe aqueous phase was dried (over anhydrous magnesium sulfate)
customthe solvent was removed by distillation under reduced pressure
customto give an oil
customThe crude product was purified by chromatography over silica gel (eluent dichloromethane)

Sources & evidence

ORD record: ord-017174899ea04691bd8dd71f6502078b
Source dataset: uspto-grants-1982_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04310347

Reaction notes

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