Trifluoromethanesulfonic anhydride → HCID 57781104, compound

HRID 1690713Notes

Reaction equation

HRID 1690713 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(N(C(C)C)CC)(C)C.[CH2:25]([N:27]([CH2:38][CH3:39])[C:28](=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35]O)[CH3:26].C(OC([N:47]1[CH:51]=[C:50]([I:52])[N:49]=[CH:48]1)=O)(C)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:25]([N:27]([CH2:38][CH3:39])[C:28](=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][N:49]1[C:50]([I:52])=[CH:51][N:47]=[CH:48]1)[CH3:26]

Participants

7

Reactant 5

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 13660025N,N-Diethyl-2-(hydroxymethyl)benzamideHCID 596566331,1-Dimethylethyl 4-iodo-1H-imidazole-1-carboxylate

Product 1

HCID 57781104HCID 57781104, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

A flask is charged with dichloromethane (200 mL) and trifluoromethanesulfonic anhydride (19.34 g, 67.20 mmol) and cooled to −78° C. A solution of diisopropylethylamine (9.57 g, 73.30 mmol) and N,N-diethyl-2-hydroxymethyl-benzamide (12.92 g, 61.09 mmol) in dichloromethane (40 mL) is added over 10 min. After 30 min, a solution of 4-iodo-imidazole-1-carboxylic acid tert-butyl ester (12.83 g, 42.76 mmol) in dichloromethane (40 mL) is added. The mixture is allowed to gradually warm overnight and after 18 h, saturated aqueous sodium bicarbonate (100 mL) is added and the mixture is stirred vigorously for 30 min. The aqueous layer is extracted with dichloromethane. The combined organic phase is dried over MgSO4, filtered through a cotton plug and concentrated in vacuo. The residue is purified by silica gel flash chromatography (dichloromethane-methanol, 49:1) to afford N,N-diethyl-2-(5-iodo-imidazol-1-ylmethyl)-benzamide; MS (ESI) m/z 384.1 (M+H).

Workup

  1. waitThe mixture is allowed to gradually warm overnight and after 18 h
  2. extractionThe aqueous layer is extracted with dichloromethane
  3. dry with materialThe combined organic phase is dried over MgSO4
  4. filtrationfiltered through a cotton plug
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel flash chromatography (dichloromethane-methanol, 49:1)

Sources & evidence

ORD record
ord-955b115f81f64e2180a5608b516dbc17
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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