Water → Trifluoroacetic anhydride

HRID 2050971Notes

Reaction equation

HRID 2050971 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3](N1C2C=CC=CC=2OCC1)=[O:4].C(Cl)Cl.ICl.S(=O)(O)[O-].[Na+].[OH2:27]>C(O)(=O)C>[F:16][C:2]([F:1])([F:15])[C:3]([O:4][C:3](=[O:4])[C:2]([F:16])([F:15])[F:1])=[O:27]

Participants

7

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 24640Iodine chlorideHCID 15171868HCID 15171868, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 9845Trifluoroacetic anhydride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of 0.5 g (2.16 mmol) of this 4-(trifluoroacetyl)-3,4-dihydro-2H-1,4-benzoxazine, 20 ml of glacial acetic acid and 5 ml of methylene chloride was cooled to 10° in an ice bath. A solution of 1 ml of iodine monochloride in 1 ml of acetic acid was added slowly over a period of 5 minutes Following the addition, the mixture was stirred for 45 minutes and was then diluted with water and a aqueous solution of sodium bisulfite. The product was extracted with ether. The extracts were washed with water, dried and evaporated. Crystallization of the residue from hexane yielded colorless crystals with m.p. 78°-80°.

Workup

  1. temperaturewas cooled to 10° in an ice bath
  2. additionthe addition
  3. extractionThe product was extracted with ether
  4. washThe extracts were washed with water
  5. customdried
  6. customevaporated
  7. customCrystallization of the residue from hexane yielded colorless crystals with m.p. 78°-80°

Sources & evidence

ORD record
ord-794a5364d8164f309a598684970b991c
Source dataset
uspto-grants-1991_05
Patent number
US05015661

Reaction notes

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