(2-Chloro-4-trifluoromethyl-phenoxy)-acetic acid → N-[3-chloro-4-(2,2-diethoxy-ethoxy)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

HRID 898519Notes

Reaction equation

HRID 898519 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[Cl:17][C:18]1[CH:19]=[C:20]([NH2:33])[CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH:26]([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29]>C1COCC1>[Cl:17][C:18]1[CH:19]=[C:20]([NH:33][C:6](=[O:8])[CH2:5][O:4][C:3]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:2]=2[Cl:1])[CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH:26]([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 59691547(2-Chloro-4-trifluoromethyl-phenoxy)-acetic acid2×HCID 688756713-Chloro-4-(2,2-diethoxy-ethoxy)-phenylamine

Product 1

HCID 68875174N-[3-chloro-4-(2,2-diethoxy-ethoxy)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.495 g (0.028 mol) of CDl was added to a solution of 6.365 g (0.025 mol) of (2-chloro-4-trifluoromethyl-phenoxy)-acetic acid (intermediate product 2b) in 100 mL abs. THF and the mixture was stirred for 30 minutes at 50° C. 6.494 g (0.025 mol) of 3-chloro-4-(2,2-diethoxy-ethoxy)-phenylamine was added and the mixture was stirred for 16 hours at RT. The reaction mixture was poured into ice water and stirred for 1 hour. The precipitate formed was filtered off, washed with water and dried at 50° C.

Workup

  1. stirringstirred for 1 hour
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried at 50° C.

Sources & evidence

ORD record
ord-b5939c03a5ba4a1d907457b04d9011d5
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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