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Water → HCID 67393523, compound

HRID 2056628
Notes
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Reaction equation

HRID 2056628 reaction equation
FC(F)(F)C(OC1C(OC(=O)C(F)(F)F)=C(I)C=CC=1)=[O:4].[F:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[C:30]1[O:31][C:32]2[C:38](N)=[C:37]([O:40][CH3:41])[CH:36]=[CH:35][C:33]=2[N:34]=1.[OH2:42]>C(#N)C.O>[F:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[C:30]1[O:42][C:35]2[C:36](=[O:4])[C:37]([O:40][CH3:41])=[CH:38][C:32](=[O:31])[C:33]=2[N:34]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 12041285BistrifluoroacetoxyiodobenzeneHCID 69219986HCID 69219986, compound

Product 1

HCID 67393523HCID 67393523, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent2×

Conditions

Temperature
-5 °C

Procedure

2.9 g (6.81 mmol; 2.2 equivalents) of bis(trifluoroacetoxy)iodo benzene dissolved in 75 ml of an acetonitrile/water mixture 4:1 is added dropwise to a solution of 0.86 g (3.10 mmol) of 2-(2,5-difluorophenyl)-6-methoxy-1,3-benzoxazol-7-amine in 30 ml of an acetonitrile/water mixture 4:1 at −5° C. After stirring for 30 minutes at −5° C., 70 ml of water is added to the reaction medium and the product formed is extracted twice with 100 ml of dichloromethane. The organic phases are combined and dried over sodium sulphate, then the solvents are evaporated off under reduced pressure. The residue is then purified by chromatography on a silica column (eluent: dichloromethane/methanol mixture 99:1) and 475 mg (yield=53%) of 2-(2,5-difluorophenyl)-6-methoxy-1,3-benzoxazole-4,7-dione is obtained in the form of a yellow powder.

Workup

  1. customthe product formed
  2. extractionis extracted twice with 100 ml of dichloromethane
  3. dry with materialdried over sodium sulphate
  4. customthe solvents are evaporated off under reduced pressure
  5. customThe residue is then purified by chromatography on a silica column (eluent: dichloromethane/methanol mixture 99:1)

Sources & evidence

ORD record
ord-ddbe0b099be647de9289ec2f7a1ab81d
Source dataset
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07335674B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes