Delta-Valerolactone → HCID 178520562, compound

HRID 1054546Notes

Reaction equation

HRID 1054546 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([NH2:10])[CH:4]=1.[C:13]1(=O)[O:18][CH2:17][CH2:16][CH2:15][CH2:14]1>Cl>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:8]=[CH:7][C:6]2[NH:9][C:13]([CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[N:10][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 10953Delta-ValerolactoneHCID 5208224-Trifluoromethyl-1,2-phenylenediamine

Product 1

HCID 178520562HCID 178520562, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-Trifluoromethyl-1,2-phenylenediamine (3 g, 17.03 mmol) and delta-valerolactone (1.78 ml, 18.74 mmol) in 4M HCl (15 ml) were heated to 110° C. for 18 h. The reaction mixture was quenched by addition to sat. NaHCO3(aq) (100 ml), and the mixture was extracted with EtOAc (3×100 ml). The combined organics were dried (MgSO4) and concentrated to afford a brown oil which was triturated with Et2O to afford 3.4 g (77.3%) of 4-(5-Trifluoromethyl-1H-benzoimidazol-2-yl)-butan-1-ol as a tan powder. MS (ESI+) for C12H13F3N2O m/z 258.95 [M+H]+; HPLC ret. time, 1.22 min. 1H NMR (500 MHz, MeOD) δ ppm 7.82 (1H, br. s.), 7.66 (1H, br. s.), 7.44-7.55 (1H, m), 3.62 (2H, t, J=6.46 Hz), 2.99 (2H, t, J=7.65 Hz), 1.89-2.00 (2H, m), 1.58-1.68 (2H, m).

Workup

  1. customThe reaction mixture was quenched by addition to sat. NaHCO3(aq) (100 ml)
  2. extractionthe mixture was extracted with EtOAc (3×100 ml)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. concentrationconcentrated
  5. customto afford a brown oil which
  6. customwas triturated with Et2O

Sources & evidence

ORD record
ord-8a67eb3d313d4f04a2d303c24557b423
Source dataset
uspto-grants-2016_07
Patent number
US09394310B2

Reaction notes

Loading…