Dichloromethane → HCID 19919837, compound

HRID 1033128Notes

Reaction equation

HRID 1033128 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.O[CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1.C(N(CC)C(C)C)(C)C.[CH2:37]([N:41]1[C:42](=[O:80])[N:43]([CH2:76][CH2:77][CH2:78][CH3:79])[C:44](=[O:75])/[C:45]/1=[CH:46]/[C:47]1[N:51]=[C:50]([CH2:52][CH2:53][CH2:54][CH3:55])[N:49](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:48]=1)[CH2:38][CH2:39][CH3:40].C(Cl)[Cl:82]>O.C(O)(=O)C>[ClH:82].[CH2:52]([C:50]1[N:51]([CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=2)[C:47](/[CH:46]=[C:45]2\[N:41]([CH2:37][CH2:38][CH2:39][CH3:40])[C:42](=[O:80])[N:43]([CH2:76][CH2:77][CH2:78][CH3:79])[C:44]\2=[O:75])=[CH:48][N:49]=1)[CH2:53][CH2:54][CH3:55]

Participants

8

Reactant 5

HCID 6344Dichloromethane3×HCID 67749Trifluoromethanesulfonic anhydrideHCID 81325Methyl 4-(hydroxymethyl)benzoateHCID 81531DiisopropylethylamineHCID 19919793HCID 19919793, compound

Product 1

HCID 19919837HCID 19919837, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of trifluoromethanesulfonic anhydride (0.094 mL, 0.56 mmol) in methylene chloride (10 mL) at -78° C. was added a solution of methyl 4-(hydroxymethyl)benzoate (0.093 g, 0.56 mmol) and N,N-diisopropylethylamine (0.098 mL, 0.56 mmol) in methylene chloride (10 mL) dropwise over 5 minutes. This solution was stirred for 15 minutes and then a solution of Z-1,3-dibutyl-5-[[2-butyl-3-(triphenylmethyl)-3H-imidazol-5-yl]methylene]-2,4-imidazolidinedione (0.330 g, 0.56 mmol) in methylene chloride (5 mL) was added dropwise. The mixture was allowed to slowly warm to room temperature within the cooling bath overnight. Glacial acetic acid (10 mL) and water (2 mL) were added and the mixture boiled for 1 hour on a steam bath. After evaporation in vacuo the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 and brine, and then dried over MgSO4. Chromatography eluting with CHCl3 afforded the required product with spectral characteristics identical with the produce formed in Example 33.

Workup

  1. waitthe mixture boiled for 1 hour on a steam bath
  2. customAfter evaporation in vacuo the residue
  3. dissolutionwas dissolved in ethyl acetate
  4. washwashed with saturated NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. washChromatography eluting with CHCl3

Sources & evidence

ORD record
ord-4f54e95ff0b44a6f9654c5351f5d91ca
Source dataset
uspto-grants-1994_05
Patent number
US05308853

Reaction notes

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