Hydrochloric Acid → HCID 136161323, compound

HRID 2182358Notes

Reaction equation

HRID 2182358 reaction equation
[CH3:1][S:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:12](COCC[Si](C)(C)C)[C:11]3[CH:21]=[CH:22][CH:23]=[CH:24][C:10]=3[N:9]=2)[CH:4]=1.Cl>CO>[CH3:1][S:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[NH:9][C:10]3[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=3[N:12]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22477746HCID 22477746, compound

Product 1

HCID 136161323HCID 136161323, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(5-methylsulfanyl-isoxazol-3-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole (160 mg, Reference Example 12), methanol (12 mL) and concentrated aqueous hydrochloric acid (2.45 mL) were heated at reflux for four hours, then cooled and then evaporated. The residue was treated with aqueous sodium bicarbonate and the mixture was extracted with ethyl acetate. The extracts were dried and then evaporated to give 2-(5-methylsulfanyl-isoxazol-3-yl)-1H-benzoimidazole (96 mg) as an off white solid, mp 179-181° C. 1H-NMR [(CD3)2SO]: δ 4.65 (s, 3H), 9.00 (s, 1H), 9.15-9.6 (m, 4H).

Workup

  1. temperaturewere heated
  2. temperatureat reflux for four hours
  3. temperaturecooled
  4. customevaporated
  5. additionThe residue was treated with aqueous sodium bicarbonate
  6. extractionthe mixture was extracted with ethyl acetate
  7. customThe extracts were dried
  8. customevaporated

Sources & evidence

ORD record
ord-21048fdd29a540b89763bfe1f1bfbb2c
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

Loading…