Chloroacetyl chloride → 7-Iodo-6-phenyl-1H-4,5-dioxa-1-aza-phenanthrene-2,8-dione

HRID 1037375Notes

Reaction equation

HRID 1037375 reaction equation
[NH2:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([C:6](=[O:20])[C:7]([I:19])=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:9]2)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].Cl[CH2:27][C:28](Cl)=[O:29]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)(Cl)Cl>[I:19][C:7]1[C:6](=[O:20])[C:5]2[C:10](=[C:11]3[C:2](=[CH:3][CH:4]=2)[NH:1][C:28](=[O:29])[CH2:27][O:12]3)[O:9][C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 670679197-Amino-8-hydroxy-3-iodo-2-phenyl-chromen-4-one

Product 1

HCID 670678277-Iodo-6-phenyl-1H-4,5-dioxa-1-aza-phenanthrene-2,8-dioneYield 99.6%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 7-amino-8-hydroxy-3-iodo-2-phenyl-chromen-4-one (150 mg, 0.40 mmol), benzyltriethylammonium chloride (91 mg, 0.40 mmol) and NaHCO3 (168 mg, 2 mmol) in CHCl3 (5 mL) at 0° C. was added a solution of chloroacetyl chloride (35 μL, 0.44 mmol) in CHCl3 (1 mL) dropwise over 30 mins. The reaction mixture was stirred at 0° C. for 2 hours before heating at 50° C. for 18 hours. The resultant mixture was cooled to RT and was partitioned between DCM and water. The aqueous phase was filtered and the solid collected and azeotroped with methanol to give the title compound as a beige solid (167 mg, 99%). LCMS (Method G): RT=3.18 min, [M+H]+=420.

Workup

  1. temperaturebefore heating at 50° C. for 18 hours
  2. customwas partitioned between DCM and water
  3. filtrationThe aqueous phase was filtered
  4. customthe solid collected
  5. customazeotroped with methanol

Sources & evidence

ORD record
ord-22c131d6879c4537a5ed3bd74d568b7b
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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