N,N-Dimethylaniline → HCID 25259881, compound

HRID 2222761Notes

Reaction equation

HRID 2222761 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH:9]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=CN=2)[C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH3:26][N:27](C)C1C=CC=CC=1.O1[CH2:40][CH2:39][N:38]([CH:41](O)[CH3:42])[CH2:37][CH2:36]1.[OH2:44]>O1CCCC1.CCOCC>[N:38]1([CH2:41][CH2:42][O:12][C:10](=[O:11])[CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:25])[F:24])[CH:4]=2)[O:13][C:14]2[CH:26]=[N:27][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=2)[CH2:39][CH2:40][O:44][CH2:36][CH2:37]1

Participants

7

Reactant 4

HCID 949N,N-DimethylanilineHCID 962WaterHCID 30293761-MorpholinoethanolHCID 25259649(3-Trifluoromethyl-phenyl)-(5-trifluoromethyl-pyridin-2-yloxy)-acetic acid

Product 1

HCID 25259881HCID 25259881, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

(3-Trifluoromethyl-phenyl)-(5-trifluoromethyl-pyridin-2-yloxy)-acetic acid, 100, prepared as described in Example 4, (0.05 mol) was converted into the acid chloride, using the procedure of Example 6. The acid chloride (0.01 mol) was dissolved in tetrahydrofuran (25 mL) and N,N-dimethylaniline (2 mL) and morpholinoethanol (2 mL) were added. The progress of the reaction was monitored by TLC. When the reaction was complete, water and ether were added. The organic phase was washed with dilute hydrochloric acid, dried and concentrated. The residue was chromatographed to afford the title compound 137.

Workup

  1. washThe organic phase was washed with dilute hydrochloric acid
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was chromatographed

Sources & evidence

ORD record
ord-367b1877cd634eac9b2e8a7e22b072de
Source dataset
uspto-grants-2008_05
Patent number
US07371888B2

Reaction notes

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