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

HRID 1600559Notes

Reaction equation

HRID 1600559 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 dimethyl-formamide (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 dimethyl-formamide (100 ml)
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d7854f4df0ef4c40aed06e16ef195687
Source dataset
uspto-grants-1999_11
Patent number
US05977028

Reaction notes

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