Dichloromethane → HCID 69054751, compound

HRID 2105981Notes

Reaction equation

HRID 2105981 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][O:11]2)[CH:7]=1.[O:21]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[NH:24][CH2:23][CH2:22]1.C(Cl)[Cl:32]>O1CCOCC1>[ClH:32].[O:21]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]([CH2:12][C:10]([OH:11])([CH2:9][C:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:19][CH3:20])([CH3:18])[CH3:17])[C:13]([F:16])([F:15])[F:14])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 5850963,4-Dihydro-2H-1,4-benzoxazineHCID 160992392-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

Product 1

HCID 69054751HCID 69054751, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (see Example 1) (0.139 g) and 3,4-dihydro-2H-benzo[1,4]oxazine (0.76 g) was dissolved in approximately 5 mL of methylene chloride and 0.55 g of flash silica gel was added. The volatiles were removed in vacuo and the residue was microwaved for 60 seconds at 150° C. and applied to a column of flash silica gel. Elution with EtOAc-hexanes (1:10) and concentration in vacuo of the product-rich fractions provided a residue which was dissolved in diethyl ether. HCl in dioxane was added. The volatiles were removed in vacuo and the residue triturated with diethyl ether. The resulting solid was dried in vacuo to provide the title compound, m.p. 98° C.-99° C.

Workup

  1. addition0.55 g of flash silica gel was added
  2. customThe volatiles were removed in vacuo
  3. customthe residue was microwaved for 60 seconds at 150° C.
  4. washElution
  5. concentrationwith EtOAc-hexanes (1:10) and concentration in vacuo of the product-rich fractions
  6. customprovided a residue which
  7. additionwas added
  8. customThe volatiles were removed in vacuo
  9. customthe residue triturated with diethyl ether
  10. customThe resulting solid was dried in vacuo

Sources & evidence

ORD record
ord-dfe380ba5e2a48eb8b773c1863dae4a6
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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