Dimethylformamide → HCID 178526025, compound

HRID 49580Notes

Reaction equation

HRID 49580 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][O:4][CH:3]1[OH:8].C(O)(=[O:11])C.[CH:13]([NH2:15])=[NH:14].C(NCC)C.CN(C)[CH:23]=[O:24]>>[C:23]([OH:24])(=[O:11])[C:3]([OH:8])=[O:4].[NH:14]1[CH:3]=[C:2]([CH2:7][CH2:6][CH2:5][OH:4])[N:15]=[CH:13]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 160693Formamidine acetateHCID 149325523-Bromooxan-2-ol

Product 1

HCID 178526025HCID 178526025, compoundYield 42%

Conditions

Temperature
80 °C

Procedure

5.0 g of 3-bromo-tetrahydropyran-2-ol prepared in Example 1 and 5.75 g of formamidine acetate were added to 25 ml of N,N-dimethylformamide and 9 ml of diethylamine was added dropwise thereto. The reaction mixture was stirred for about 4 hours at 80° C. and distilled in vacuo for about 1 hour at the same temperature to remove the solvent. The resulting oily residue was diluted with 25 ml of acetone and 4.97 g of oxalic acid was slowly added thereto for crystallization. The reaction mixture was stirred for about 1 hour, filtered, and washed with acetone to give 2.5 g of 3-(1H-imidazol-4-yl)propanol oxalate (yield: 42%).

Workup

  1. additionwas added dropwise
  2. distillationdistilled in vacuo for about 1 hour at the same temperature
  3. customto remove the solvent
  4. additionThe resulting oily residue was diluted with 25 ml of acetone and 4.97 g of oxalic acid
  5. additionwas slowly added
  6. customfor crystallization
  7. stirringThe reaction mixture was stirred for about 1 hour
  8. filtrationfiltered
  9. washwashed with acetone

Sources & evidence

ORD record
ord-9a9397b2893444ecba60977b34c36ef4
Source dataset
uspto-grants-2004_03
Patent number
US06706888B2

Reaction notes

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