Triethylamine → 2,4-Di[(1,1-dimethylethyl)carbonylamino]-6-(3-trifluoromethylphenylmethoxyimino)-5,6,7,8-tetrahydroquinazoline

HRID 727207Notes

Reaction equation

HRID 727207 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.[F:27][C:28]([F:39])([F:38])[C:29]1[CH:30]=[C:31]([CH2:35][O:36][NH2:37])[CH:32]=[CH:33][CH:34]=1.C(N(CC)CC)C>C(O)C>[CH3:3][C:2]([C:5]([NH:7][C:8]1[N:17]=[C:16]([NH:18][C:19]([C:21]([CH3:22])([CH3:23])[CH3:24])=[O:20])[C:15]2[CH2:14][C:13](=[N:37][O:36][CH2:35][C:31]3[CH:32]=[CH:33][CH:34]=[C:29]([C:28]([F:27])([F:39])[F:38])[CH:30]=3)[CH2:12][CH2:11][C:10]=2[N:9]=1)=[O:6])([CH3:4])[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 203812O-((3-(Trifluoromethyl)phenyl)methyl)hydroxylamine--hydrogen chloride (1/1)HCID 197051902,4-Di[(1,1-dimethylethyl)carbonylamino]-5,6,7,8-tetrahydro-6-quinazolinone

Product 1

HCID 542317742,4-Di[(1,1-dimethylethyl)carbonylamino]-6-(3-trifluoromethylphenylmethoxyimino)-5,6,7,8-tetrahydroquinazoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This compound is prepared in a manner analogous to that of Step E of Example 12, using 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 Example 12) and 2.7 grams (0.012 mole) of O-(3-trifluoromethylphenylmethyl)hydroxylamine hydrochloride in about 45 mL of ethanol. This preparation differs from Step E of Example 12 in that prior to heating at reflux for four hours, 1.5 grams (0.01 5 mole) of triethylamine is added as an acid acceptor, yielding 2,4-di[(1,1-dimethylethyl)carbonylamino]-6-(3-trifluoromethylphenylmethoxyimino)-5,6,7,8-tetrahydroquinazoline.

Workup

  1. customThis compound is prepared in a manner analogous to that of Step E of Example 12
  2. temperatureto heating
  3. temperatureat reflux for four hours

Sources & evidence

ORD record
ord-5e1588458d0148cd900c8b305f1b3c0c
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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