Water → 6-(4-Phenyl-2-quinazolinyloxy)hexanoic acid

HRID 2396524Notes

Reaction equation

HRID 2396524 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O-:9])=[O:8].[K+].[H-].[Na+].Cl[C:14]1[N:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.O>S1(CCCC1C([O-])=O)(=O)=O.C(O)(=O)C>[C:24]1([C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])[N:23]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 31235822-Chloro-4-phenylquinazolineHCID 2371282621810-34-4

Product 1

HCID 189872436-(4-Phenyl-2-quinazolinyloxy)hexanoic acidYield 11.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 86748276SulfolaneatSolvent

Procedure

To a suspension of 1.74 g of potassium 6-hydroxyhexanoate (prepared from e-caprolactone) in 35 cc of sulfolaneat 60° C. was added 0.64 g of sodium hydride (55 % w/w dispersion in mineral oil). The mixture was stirred for 30 minutes to 140° C. until effervescence had stopped. 3 g of 2-chloro-4-phenyl-quinazoline were then added and the resultant mixture was heated for further 2 hours to 140° C. The mixture was poured into 500 cc of water, neutralized with acetic acid and extracted with dichloromethane (3#300 cc). The combined extracts were washed with water, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel (50-200 mm; eluent: 95:5 diethyl ether/methanol), then washed with n-hexane and filtered to give 0.4 g (10%) of 6-(4-phenyl-2-quinazolinyloxy)hexanoic acid as a whitish solid. (m.p.=112°-114° C.)

Workup

  1. extractionextracted with dichloromethane (3#300 cc)
  2. washThe combined extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (50-200 mm; eluent: 95:5 diethyl ether/methanol)
  6. washwashed with n-hexane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-254daad2651a4ef6ba1f0aa50e5703ee
Source dataset
uspto-grants-1996_02
Patent number
US05492915

Reaction notes

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