Water → HCID 22909977, compound

HRID 1379286Notes

Reaction equation

HRID 1379286 reaction equation
[I-].[Na+].[CH2:3]([NH2:5])[CH3:4].[Br:6][C:7]1[CH:8]=[C:9]([N:14]2[CH2:18][CH2:17][CH:16](OS(C)(=O)=O)[C:15]2=[O:24])[CH:10]=[CH:11][C:12]=1[F:13].O>O1CCCC1>[Br:6][C:7]1[CH:8]=[C:9]([N:14]2[CH2:18][CH2:17][CH:16]([NH:5][CH2:3][CH3:4])[C:15]2=[O:24])[CH:10]=[CH:11][C:12]=1[F:13]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6341EthylamineHCID 22909964HCID 22909964, compound

Product 1

HCID 22909977HCID 22909977, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium iodide (1.1 g), followed by ethylamine (1.92 ml) was added to a solution in tetrahydrofuran (60 ml) of the ethylamino compound prepared in Step 2 (2.6 g). The solution was stirred for two hours and then left to stand overnight. The reaction mixture was then poured into water and extracted with ethyl acetate three times. The extracts were combined, washed twice with water and once with brine, dried (magnesium sulphate), and concentrated to yield a dark brown oil. This was chromatographed on a silica column using a mixture of triethylamine and ethyl acetate (1:9) as the eluent. The title compound was obtained as a yellow solid. The NMR spectrum was consistent with the expected structure.

Workup

  1. waitleft
  2. waitto stand overnight
  3. extractionextracted with ethyl acetate three times
  4. washwashed twice with water and once with brine
  5. dry with materialdried (magnesium sulphate)
  6. concentrationconcentrated
  7. customto yield a dark brown oil
  8. customThis was chromatographed on a silica column
  9. additiona mixture of triethylamine and ethyl acetate (1:9) as the eluent

Sources & evidence

ORD record
ord-0c31643e9a5d49a8a3295234285d092a
Source dataset
uspto-grants-1997_09
Patent number
US05670656

Reaction notes

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