Hydroxylamine → HCID 86098714, compound

HRID 2359887Notes

Reaction equation

HRID 2359887 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][N:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]1SC.[NH2:22][OH:23]>C(O)(C)C>[OH:23][NH:22][C:7]1[N:6]([CH2:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]=2[O:2][CH3:1])[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 68546169HCID 68546169, compound

Product 1

HCID 86098714HCID 86098714, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

0.6 g (2.01 mmol) 3-(2-methoxybenzyl)-2-(methylthio)-3,4-dihydroquinazoline and 265 mg hydroxylamine in 10 mL isopropanol were heated at reflux for approx. 36 hours. For workup, the mixture was evaporated, the resulting residue was recrystallized in a mixture of diethyl ether/methyl tert-butyl ether 1:1 and then lyophilized by MPLC (silica gel: Bischoff Prontoprep 60-2540-C18E, 32 μm; mobile phase: CH3CN/H2O+0.1% acetic acid). 300 mg white solids.

Workup

  1. temperatureat reflux for approx. 36 hours
  2. customFor workup, the mixture was evaporated
  3. customthe resulting residue was recrystallized in a mixture of diethyl ether/methyl tert-butyl ether 1:1

Sources & evidence

ORD record
ord-a8b693bc69454def8295d52960a26b28
Source dataset
uspto-grants-2014_04
Patent number
US08686002B2

Reaction notes

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