Hydrochloric Acid → HCID 68833585, compound

HRID 227578Notes

Reaction equation

HRID 227578 reaction equation
[CH3:1][C:2]1[C:6]2[NH:7][C:8](=O)[O:9][C:10](=[O:11])[C:5]=2[S:4][CH:3]=1.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:23]=[CH:22][C:18](C(Cl)=O)=[CH:17][CH:16]=1.Cl>CN(C)C1C=CN=CC=1.O1CCOCC1>[CH3:1][C:2]1[C:6]2[N:7]=[C:8]([C:18]3[CH:22]=[CH:23][C:15]([C:14]([F:25])([F:24])[F:13])=[CH:16][CH:17]=3)[O:9][C:10](=[O:11])[C:5]=2[S:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 57437975HCID 57437975, compound

Product 1

HCID 68833585HCID 68833585, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent

Procedure

4-(Dimethylamino)pyridine (0.66 g, 5.41 mmol) was added to the product from Step A in dioxane (10 mL). 4-(Trifluoromethyl)benzoyl chloride (1.13 g, 5.42 mmol) was added to the mixture and the mixture was boiled for approximately 3 hours. The mixture was allowed to cool to room temperature and was poured into hydrochloric acid (100 mL, 1 N). The mixture was extracted with ethyl acetate (3×50 mL) and the combined extracts were dried and evaporated. Chromatography on silicon gel (eluted with ethyl acetate/hexanes) gave the product as a white solid 1.56 g, (91.7%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  2. customthe combined extracts were dried
  3. customevaporated

Sources & evidence

ORD record
ord-8d0ddfc2fb7b4130acced0ca13dfbde6
Source dataset
uspto-grants-2009_07
Patent number
US07560564B2

Reaction notes

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