Dichloromethane → HCID 15171865, compound

HRID 256859Notes

Reaction equation

HRID 256859 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-29e03681d4c6484fa25a43154091ea16
Source dataset
uspto-grants-1993_11
Patent number
US05260294

Reaction notes

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