HCID 18402977, compound → HCID 18402946, compound

HRID 1953985Notes

Reaction equation

HRID 1953985 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:6][C:5]([NH:19][C:20](=[O:25])[CH2:21][NH:22][CH2:23][CH3:24])=[C:4]([F:26])[CH:3]=1.[CH3:27][OH:28].C(Cl)Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([O:8][C:9]2[C:14]([C:15]([F:16])([F:18])[F:17])=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:6][C:5]([N:19]2[C:20](=[O:25])[CH2:21][N:22]([CH2:23][CH3:24])[C:27]2=[O:28])=[C:4]([F:26])[CH:3]=1

Participants

4

Reactant 2

HCID 18402977HCID 18402977, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 18402946HCID 18402946, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N-[4-chloro-2-fluoro-5-(3-trifluoromethyl-2-pyridyloxy)phenyl]-2-ethylaminoacetamide (0.82 g) and 1,11 -carbonyldiimidazole (0.43 g) in toluene (20 ml) was heated at reflux for 2 hours, cooled and processed. Column chromatography on silica gel eluting with 2.5% methanol-methylene chloride gave a buff colored solid (0.8 g), mp 162-3° C. 1H NMR (CDCl3, TMS): 1.24(3H, t, J=7 Hz), 3.53(2H, q, J=7 Hz), 4.05(2H, s), 7.13(1H, m), 7.30(1H, d, J=7 Hz), 7.38(1H, d, J=9 Hz), 8.01(1H, m), 8.24(1H, m).

Workup

  1. temperatureat reflux for 2 hours
  2. temperaturecooled

Sources & evidence

ORD record
ord-5e085189862f4319a93592a9e5aa964b
Source dataset
uspto-grants-2000_09
Patent number
US06121201

Reaction notes

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