Ethyl Acetate → HCID 18614754, compound

HRID 1265182Notes

Reaction equation

HRID 1265182 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([Cl:16])[C:7]=1[N:17]1[CH:21]=[C:20]2[CH:22](O)[CH2:23][CH2:24][C:19]2=[N:18]1.CCOC(C)=O.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([Cl:16])[C:7]=1[N:17]1[CH:21]=[C:20]2[CH:22]([Cl:3])[CH2:23][CH2:24][C:19]2=[N:18]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 18614744HCID 18614744, compound

Product 1

HCID 18614754HCID 18614754, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thionyl chloride (0.1 mL, 1.37 mmol) was added to a solution of (62) (100.0 mg, 0.29 mmol) in THF (2 mL). After stirring for 2 hours at ambient temperature, EtOAc (10 mL) was added and the resulting mixture was poured into 5% aq. NaHCO3 (20 mL) at 4° C. The resulting mixture was extracted with EtOAc (10 mL). The organic layer was washed with 5% NaHCO3 (20 mL) at 4° C., dried (Na2SO4) and concentrated in vacuo to give the title compound as a pale solid in quantitative yield. 1H NMR (CDCl3); δ 7.72 (s, 2H), 7.42 (s, 1H), 5.43 (d, 1H, J=5.6), 3.22-2.94 (m, 2H), 2.85-2.70 (m, 2H); MS (M++1) 355.4.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (10 mL)
  2. washThe organic layer was washed with 5% NaHCO3 (20 mL) at 4° C.
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29a24f24b5f640208528f474700640ad
Source dataset
uspto-grants-2003_04
Patent number
US06545033B1

Reaction notes

Loading…