Chlorine → N-(4-chloro-2'-fluoro-5'-propargyloxyphenyl)-3-(trifluoromethyl)glutaramic acid

HRID 275428Notes

Reaction equation

HRID 275428 reaction equation
[F:1][C:2]([F:12])([F:11])[CH:3]1[CH2:9][C:8](=[O:10])[O:7][C:5](=[O:6])[CH2:4]1.ClCl.[Cl:15][C:16]1[C:22]([O:23][CH2:24][C:25]#[CH:26])=[CH:21][C:19]([NH2:20])=[C:18]([F:27])[CH:17]=1>C(Cl)Cl>[Cl:15][C:16]1[C:22]([O:23][CH2:24][C:25]#[CH:26])=[CH:21][C:19]([NH:20][C:8](=[O:10])[CH2:9][CH:3]([C:2]([F:1])([F:12])[F:11])[CH2:4][C:5]([OH:7])=[O:6])=[C:18]([F:27])[CH:17]=1

Participants

5

Reactant 3

HCID 24526Chlorine2×HCID 13272927Benzenamine, 4-chloro-2-fluoro-5-(2-propynyloxy)-HCID 157442444-(Trifluoromethyl)dihydro-2H-pyran-2,6(3H)-dione

Product 1

HCID 15767068N-(4-chloro-2'-fluoro-5'-propargyloxyphenyl)-3-(trifluoromethyl)glutaramic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 1 liter three-necked round-bottomed flask equipped with overhead stirrer, dropping funnel, thermometer and nitrogen (N2) inlet were placed 3-(trifluoromethyl)glutaric anhydride (18.2 g, 0.100 tool) and methylene chloride (CH2 -Cl2) (250 ml). The mixture was stirred to homogeneity and a solution of 4-chloro-2-fluoro-5-propargyloxyaniline (19.9 g, 0.100 mol) in CH2 -Cl2 (50 ml) was added dropwise over 10 minutes to give a clear solution. The mixture was stirred overnight at ambient temperature, during which time a thick white precipitate was formed.

Workup

  1. customInto a 1 liter three-necked round-bottomed flask equipped with overhead stirrer
  2. customthermometer and nitrogen (N2) inlet were placed
  3. customto give a clear solution
  4. stirringThe mixture was stirred overnight at ambient temperature, during which time a thick white precipitate
  5. customwas formed

Sources & evidence

ORD record
ord-a436235ab85b4a72ad2c11f67e8a6da2
Source dataset
uspto-grants-1995_02
Patent number
US05393735

Reaction notes

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