Hydrochloric Acid → HCID 58474435, compound

HRID 1400845Notes

Reaction equation

HRID 1400845 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[S:20][C:19]3[C:14](=[N:15][CH:16]=[CH:17][C:18]=3[O:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:23]=3[F:31])[CH:13]=2)[CH:9]=[N:8]1.Cl>C1COCC1>[F:31][C:23]1[CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[CH:26]=[CH:27][C:22]=1[O:21][C:18]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:13]=[C:12]([C:10]3[CH:9]=[N:8][N:7]([CH2:6][CH:2]=[O:1])[CH:11]=3)[S:20][C:19]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58474722HCID 58474722, compound

Product 1

HCID 58474435HCID 58474435, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 145 (900 mg, 2.034 mmol) in THF (20 mL) was added 3M HCl (30 mL) and the reaction mixture was heated to reflux for 24 hours. The mixture was cooled to RT, and concentrated. The residual aqueous solution was treated with solid sodium bicarbonate and then extracted with DCM. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated. The crude aldehyde 146 (810 mg, 100% yield) was used in the next step with no additional purification. MS (m/z)=399.3 (M+H)

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 24 hours
  3. concentrationconcentrated
  4. additionThe residual aqueous solution was treated with solid sodium bicarbonate
  5. extractionextracted with DCM
  6. customThe organic phase was collected
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6f5908c8801e48049590dba049b1c422
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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