Hydrochloric Acid → HCID 90280247, compound

HRID 2170393Notes

Reaction equation

HRID 2170393 reaction equation
[Cl:1][C:2]1[C:3]([C:10](N(OC)C)=[O:11])=[N:4][CH:5]=[C:6]([S:8][CH3:9])[N:7]=1.CC(C[AlH]CC(C)C)C.Cl>C1COCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH:10]=[O:11])=[N:4][CH:5]=[C:6]([S:8][CH3:9])[N:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 90280232HCID 90280232, compound

Product 1

HCID 90280247HCID 90280247, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of 55C (750 mg, 3.03 mmol) in THF at 78° C., DIBAL-H (3.33 mL, 3.33 mmol) in toluene was added to the solution slowly. Then, it was stirred for 2 hours at 78° C. HCl (4 mL, 1 N) was added to the solution and warmed to 0° C. The mixture was stirred for 20 minutes at 0° C. then extracted with EtOAc twice. The organic layer was dried and concentrated to provide the crude product which was used without further purification. MS (m/z) 189 [M+H]+.

Workup

  1. temperaturewarmed to 0° C
  2. stirringThe mixture was stirred for 20 minutes at 0° C.
  3. extractionthen extracted with EtOAc twice
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-181c9f2a0f164d5bb27e8f70f8ee43c2
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

Loading…