Ammonia → HCID 86751869, compound

HRID 725265Notes

Reaction equation

HRID 725265 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12](Cl)=[O:13])[CH:5]=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].[NH3:22]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([NH2:22])=[O:13])[CH:5]=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 20548185HCID 20548185, compound

Product 1

HCID 86751869HCID 86751869, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
5 °C

Procedure

Into a 3 neck round bottom flask fitted with condenser and dropping funnel was added 3-(2-chloro-α,α,α-trifluoro-4-tolyloxy) benzoyl chloride (19.8 g 0.059 mol) and toluene (80 ml). The mixture was cooled in an ice bath to about 5° C. then ammonia solution 32% (15.6 g, 0.29 mol) was added dropwise. A yellow/orange precipitate formed and the mixture was stirred vigorously for 3 hours. The mixture was then extracted with toluene (200 ml) and washed with water (80 ml). The organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo. The resulting solid was then triturated with hexane to afford the product as a white solid (16.5 g, 91%). IR 1652 cm-1 (amide C=O), 3376 and 3191 cm-1 (N--H str);

Workup

  1. customInto a 3 neck round bottom flask fitted with condenser
  2. customA yellow/orange precipitate formed
  3. extractionThe mixture was then extracted with toluene (200 ml)
  4. washwashed with water (80 ml)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe resulting solid was then triturated with hexane

Sources & evidence

ORD record
ord-4f56f17749eb45b0be05503955907286
Source dataset
uspto-grants-1998_01
Patent number
US05705691

Reaction notes

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