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Hydrochloric Acid → 3-[3-(6-Hydroxy-m-tolyl)-1,2-benzisoxazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

HRID 1274551
Notes
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Reaction equation

HRID 1274551 reaction equation
C[O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[C:14]3[CH:15]=[C:16]([N:19]4[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]4=[O:31])[CH:17]=[CH:18][C:13]=3[O:12][N:11]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.Cl>C(Cl)Cl.CC(C)=O>[OH:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[C:14]3[CH:15]=[C:16]([N:19]4[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]4=[O:31])[CH:17]=[CH:18][C:13]=3[O:12][N:11]=2)=[CH:5][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromide2×HCID 700990493-[3-(6-Methoxy-m-tolyl)-1,2-benzisoxazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 1363337213-[3-(6-Hydroxy-m-tolyl)-1,2-benzisoxazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 2

HCID 180
Acetone
Solvent
HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

A mixture of 3-[3-(6-methoxy-m-tolyl)-1,2-benzisoxazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (5.00 g, 0.0116 mol) in methylene chloride is cooled to -10° C., treated dropwise with 15.1 mL of 1 M boron tribromide in methylene chloride while maintaining the reaction mixture temperature at -15° C. to 0° C., warmed to room temperature, treated dropwise with 5 mL of the boron tribromide solution, stirred at room temperature for one hour, and poured into dilute hydrochloric acid. The resultant aqueous mixture is diluted with acetone, concentrated In vacuo, diluted with water, and filtered to obtain a solid. The solid is washed with water and dried in a vacuum oven at 60° C. to give the title product as a yellow solid which is identified by mass spectral analysis.

Workup

  1. temperaturewhile maintaining the reaction mixture temperature at -15° C. to 0° C.
  2. temperaturewarmed to room temperature
  3. concentrationconcentrated In vacuo
  4. additiondiluted with water
  5. filtrationfiltered
  6. customto obtain a solid
  7. washThe solid is washed with water
  8. customdried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-9eedda6a491d4e08a95c44028e909775
Source dataset
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06156700

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes