Acetic Acid Mixture with Hydrobromic Acid → HCID 178425725, compound

HRID 873787Notes

Reaction equation

HRID 873787 reaction equation
[C:1]1([CH3:33])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[O:9][CH2:10][C:11]([NH:13][C:14]1[NH:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25]CC2C=CC=CC=2)[N:18]=1)=[O:12].Br.C(O)(=O)C>C(Cl)(Cl)Cl>[OH:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:17]1[N:18]=[C:14]([NH:13][C:11](=[O:12])[CH2:10][O:9][C:2]2[C:1]([CH3:33])=[CH:6][C:5]([CH3:7])=[CH:4][C:3]=2[CH3:8])[NH:15][CH:16]=1

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 178425724HCID 178425724, compound2×

Product 1

HCID 178425725HCID 178425725, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To 2-(mesityloxy)-N-[4-(2-benzyloxyphenyl)-1H-imidazol-2-yl]acetamide (Compound 1) (530 mg; 1.2 mmol) obtained in Example 1, 25% hydrobromic acid/acetic acid solution (8.0 mL) was added, and the mixture was stirred for 1 hour at 60° C. To the reaction solution, chloroform (100 mL) was added, and the mixture was washed with saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, and then distilled under reduced pressure. The resulting crystals were dispersed in diethyl ether, collected by filtration and dried to give 180 mg of the title compound (yield 43%) expressed by the following formula (Ex. 2).

Workup

  1. additionwas added
  2. washthe mixture was washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. additionThe resulting crystals were dispersed in diethyl ether
  6. filtrationcollected by filtration
  7. customdried

Sources & evidence

ORD record
ord-cf47fe2f9fe14efbaf624a24f1a86391
Source dataset
uspto-grants-2015_03
Patent number
US08975411B2

Reaction notes

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