Hydrochloric Acid → HCID 178441852, compound

HRID 2225179Notes

Reaction equation

HRID 2225179 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[OH-].[Na+].[C:17](Cl)(=O)[CH2:18][CH2:19][CH2:20][CH3:21].Cl>C1COCC1>[CH2:18]([C:17]1[N:6]=[C:4]([OH:5])[C:3]2[C:2](=[CH:10][CH:9]=[C:8]([C:11]([F:12])([F:13])[F:14])[CH:7]=2)[N:1]=1)[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 61186Valeryl chloride2×HCID 210882212-Amino-5-(trifluoromethyl)benzamide

Product 1

HCID 178441852HCID 178441852, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Preparation D11, Step 1: 2-amino-5-(trifluoromethyl)-benzamide (100 mg, 0.49 mmol, 1 eq) was suspended in THF (5 mL) at 0° C. then 1.000N NaOH (0.73 mL, 0.735 mmol, 1.5 eq) was added. Valeryl chloride (87 μL, 0.735 mmol, 1.5 eq) was slowly dripped into the mixture. After 4 hours, little reaction. Added more 1.000N NaOH (5.84 mL, 5.88 mmol, 12 eq) followed by more valeryl chloride (0.70 mL, 5.88 mmol, 12 eq). After the reaction was complete, added conc. HCl until pH=3. Stripped off the THF. Extracted the aqueous 3 times with ethyl acetate. The organic layers were combined, dried (sodium sulfate) and stripped to give an oil. Purified over silica gel in 9:1 to 1:1 hexanes/ethyl acetate to give 2-butyl-6-(trifluoromethyl)quinazolin-4-ol (110 mg) as a white solid. Yield=78%. LCMS detects (M+H)+=271.21.

Workup

  1. customPreparation D11, Step 1
  2. customlittle reaction
  3. extractionExtracted the aqueous 3 times with ethyl acetate
  4. dry with materialdried (sodium sulfate)
  5. customto give an oil
  6. customPurified over silica gel in 9:1 to 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-cb34f41b540a41ed9cffe6e24a4ee5e4
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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