Acetic Acid → HCID 86732540, compound

HRID 623307Notes

Reaction equation

HRID 623307 reaction equation
[Cl:1][C:2]1[C:3]([CH2:12][CH:13]=[N:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:25])([F:24])[F:23])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:27]([OH:30])(=[O:29])[CH3:28]>>[C:27]([O:30][CH:13]([NH:14][C:15](=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([F:23])([F:24])[F:25])[CH2:12][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:5][N:4]=1)(=[O:29])[CH3:28]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 86732538HCID 86732538, compound

Product 1

HCID 86732540HCID 86732540, compoundYield 24%

Procedure

0.16 g of N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethylidene}-2-(trifluoromethyl)benzamide (Int-6) were diluted in 2 mL of acetic acid. The reaction mixture was stirred for two days at room temperature and then heated to 90° C. for one day and left at room temperature for four days. After concentration in vacuo, the crude product was purified by chromatography on silica gel to yield 0.045 g (24%) of desired product 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-1-{[2-(trifluoromethyl)benzoyl]amino}ethyl acetate (Ia-112), [M+1]=455.

Workup

  1. temperatureheated to 90° C. for one day
  2. waitleft at room temperature for four days
  3. concentrationAfter concentration in vacuo
  4. customthe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-233d5483555847c5ab0ed247dba736f8
Source dataset
uspto-grants-2016_04
Patent number
US09301526B2

Reaction notes

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