Hydrochloric Acid → HCID 136161323, compound

HRID 2064600Notes

Reaction equation

HRID 2064600 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-f154fca31b3b4c679f0e13213228440f
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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