Acetonitrile → HCID 66688783, compound

HRID 337098Notes

Reaction equation

HRID 337098 reaction equation
[CH2:1]([C:3]([CH2:21][CH3:22])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C(N)=O)[CH3:2].FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.C(#[N:46])C>O>[CH2:1]([C:3]([CH2:21][CH3:22])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH2:46])[CH3:2]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 102317Bis(trifluoroacetoxy)iodobenzene2×HCID 66688579HCID 66688579, compound

Product 1

HCID 66688783HCID 66688783, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of α,α-diethyl-2-(phenylmethoxy)-benzeneacetamide (Example 266c, 0.77 g) in acetonitrile (6 mL) and water (6 mL) was treated with (bis(trifluoroacetoxy)iodo)benzene (1.113 g) under nitrogen and the reaction stirred at room temperature for 16 h. Further (bis(trifluoroacetoxy)iodo)benzene (1.0 g) was added and the reaction stirred for 3 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and evaporated. The crude product was purified on SCX resin eluting with methanol (discarded) followed by 7N NH3 in methanol. The basic fractions were collected and the volatiles were removed in vacuo to afford subtitle compound (0.83 g).

Workup

  1. stirringthe reaction stirred for 3 h
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified on SCX resin
  7. washeluting with methanol (discarded)
  8. customThe basic fractions were collected
  9. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-3b50a6e501f6401f856c6f386a13c125
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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