Dichloromethane → HCID 15171865, compound

HRID 654507Notes

Reaction equation

HRID 654507 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][CH2:6]1)=[O:4].C(Cl)Cl.[I:20]Cl.S(=O)(O)[O-].[Na+]>C(O)(=O)C.O>[F:16][C:2]([F:1])([F:15])[C:3]([N:5]1[C:10]2[CH:11]=[C:12]([I:20])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][CH2:6]1)=[O:4]

Participants

7

Reactant 4

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

Product 1

HCID 15171865HCID 15171865, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

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-f8253b6f1df2413cb5e0aad7dbd0d01b
Source dataset
uspto-grants-1992_07
Patent number
US05132310

Reaction notes

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