Iodine chloride → 7-fluoro-6-iodo-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 277667Notes

Reaction equation

HRID 277667 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[I:13]Cl.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[I:13][C:12]1[C:2]([F:1])=[CH:3][C:4]2[O:9][CH2:8][C:7](=[O:10])[NH:6][C:5]=2[CH:11]=1

Participants

5

Reactant 3

HCID 24640Iodine chlorideHCID 137312957-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 23665763Sodium Bisulfite

Product 1

HCID 226256087-fluoro-6-iodo-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 94.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-Fluoro-2H-1,4-benzoxazin-3(4H)-one (15.8 g) was mixed with iodine monochloride (15.6 g) in acetic acid (150 ml) and heated to reflux for 36 h. The cooled mixture was treated with saturated aqueous sodium bisulfite until the color was dissipated. The solid was filtered and washed well with water. The solid was air dried and dried further by dissolution in dimethylformamide (100 ml) and evaporated to dryness under reduced pressure to give the desired product (26.3 g) contaminated with some starting material. (The reaction can be taken to completion by addition of more iodine monochloride and refluxing for 24 h longer.) The crude product was used in Step B.

Workup

  1. temperatureheated
  2. temperatureto reflux for 36 h
  3. filtrationThe solid was filtered
  4. washwashed well with water
  5. customdried
  6. dry with materialdried further by dissolution in dimethylformamide (100 ml)
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e41b3f56f6d64b44836610ae62f0fc1c
Source dataset
uspto-grants-2002_03
Patent number
US06358885B1

Reaction notes

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