O-(3,5-Dichlorophenyl)hydroxylamine → 2,4-Di[(1,1-dimethylethyl)carbonylamino]-6-(3,5-dichlorophenoxyimino)-5,6,7,8-tetrahydroquinazoline

HRID 1735338Notes

Reaction equation

HRID 1735338 reaction equation
[CH3:1][C:2]([C:5]([NH:7][C:8]1[N:17]=[C:16]([NH:18][C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])=[O:20])[C:15]2[CH2:14][C:13](=O)[CH2:12][CH2:11][C:10]=2[N:9]=1)=[O:6])([CH3:4])[CH3:3].[Cl:26][C:27]1[CH:28]=[C:29]([O:34][NH2:35])[CH:30]=[C:31]([Cl:33])[CH:32]=1>C(O)C>[CH3:4][C:2]([C:5]([NH:7][C:8]1[N:17]=[C:16]([NH:18][C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])=[O:20])[C:15]2[CH2:14][C:13](=[N:35][O:34][C:29]3[CH:28]=[C:27]([Cl:26])[CH:32]=[C:31]([Cl:33])[CH:30]=3)[CH2:12][CH2:11][C:10]=2[N:9]=1)=[O:6])([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 11736040O-(3,5-Dichlorophenyl)hydroxylamineHCID 197051902,4-Di[(1,1-dimethylethyl)carbonylamino]-5,6,7,8-tetrahydro-6-quinazolinone

Product 1

HCID 536722812,4-Di[(1,1-dimethylethyl)carbonylamino]-6-(3,5-dichlorophenoxyimino)-5,6,7,8-tetrahydroquinazoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 3.5 grams (0.010 mole) of 2,4-di[(1,1-dimethylethyl)carbonylamino]-5,6,7,8-tetrahydro-6-quinazolinone (prepared in Step C of this Example) in 30 mL of ethanol is stirred, and a solution of 2.1 grams (0.012 mole) of O-(3,5-dichlorophenyl)hydroxylamine in 15 mL of ethanol is added dropwise. Upon completion of addition, the reaction mixture is heated to reflux, where it is stirred for about four hours. After this time the reaction mixture is cooled and concentrated under reduced pressure to a residue. The residue is dissolved in diethyl ether and washed with two portions of an aqueous solution saturated with sodium chloride. The organic layer is dried with sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 2,4-di[(1,1-dimethylethyl)carbonylamino]-6-(3,5-dichlorophenoxyimino)-5,6,7,8-tetrahydroquinazoline.

Workup

  1. additionUpon completion of addition
  2. temperaturethe reaction mixture is heated
  3. temperatureto reflux
  4. stirringwhere it is stirred for about four hours
  5. temperatureAfter this time the reaction mixture is cooled
  6. concentrationconcentrated under reduced pressure to a residue
  7. dissolutionThe residue is dissolved in diethyl ether
  8. washwashed with two portions of an aqueous solution saturated with sodium chloride
  9. dry with materialThe organic layer is dried with sodium sulfate
  10. filtrationfiltered
  11. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-3bd588a8d9b24f98adf60ca79ede0106
Source dataset
uspto-grants-1996_07
Patent number
US05536725

Reaction notes

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