Hydrochloric Acid → HCID 23509862, compound

HRID 1883507Notes

Reaction equation

HRID 1883507 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.Cl.N([O-])=O.[Na+].[Na].C(OC(=S)[SH:33])C.[OH-].[Na+]>O.C(OCC)(=O)C>[SH:33][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 8823Ethyl xanthateHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 23509923HCID 23509923, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23509862HCID 23509862, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-(4-amino-phenyl)-2-(3-trifluoromethyl-phenyl)-propionic acid (4.0 g, 12.9 mmol) in water (50 ml) and hydrochloric acid (2.8 ml, 32.3 mmol) at 0-5° C. was added sodium nitrite (0.89 g, 12.9 mmol) in water (20 ml). The reaction mixture was warmed to room temperature and poured in a solution of the sodium salt of dithiocarbonic acid O-ethyl ester (4.14 g, 25.8 mmol) in water (20 ml). The reaction mixture was stirred at 60° C. for 2 hours and the precipitate (resin) was solved with ethyl acetate. The organic layer was washed with water, dried, and evaporated in vacuo. The resulting dark brown oil was solved in ethanol (50 ml). At refluxing temperature, sodium hydroxide (3.6 g, 64.5 mmol) was added. After three hours at that temperature, the ethanol was removed, the residue solved in water, and the aqueous layer washed with dichloromethane. To the aqueous layer, potassium hydrogensulfate (10 g) was added. The resulting oil was extracted with dichloromethane, dried, and evaporated in vacuo to give 3.05 g (72%) of the desired product. MS m/z: 327.2 (M+H)+.

Workup

  1. washThe organic layer was washed with water
  2. customdried
  3. customevaporated in vacuo
  4. additionwas added
  5. waitAfter three hours at that temperature
  6. customthe ethanol was removed
  7. washthe aqueous layer washed with dichloromethane
  8. additionTo the aqueous layer, potassium hydrogensulfate (10 g) was added
  9. extractionThe resulting oil was extracted with dichloromethane
  10. customdried
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-0a211a2fbcec48c78b2f78cb6b2d6cc0
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

Loading…