Methylamine → N-methyl 4-[4-(2-chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenamide

HRID 647381Notes

Reaction equation

HRID 647381 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:20]=[CH:19][C:8]([O:9][CH:10]([CH3:18])[C:11]([O:16][CH3:17])=[CH:12][C:13](Cl)=[O:14])=[CH:7][CH:6]=1.[CH3:29][NH2:30]>C1COCC1>[CH3:29][NH:30][C:13](=[O:14])[CH:12]=[C:11]([O:16][CH3:17])[CH:10]([O:9][C:8]1[CH:19]=[CH:20][C:5]([O:4][C:3]2[CH:21]=[CH:22][C:23]([C:25]([F:28])([F:27])[F:26])=[CH:24][C:2]=2[Cl:1])=[CH:6][CH:7]=1)[CH3:18]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 570969654-[4-(2-Chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoyl chloride

Product 1

HCID 54331689N-methyl 4-[4-(2-chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[4-(2-chloro-4-trifluoromethylphenoxy) phenoxy]-3-methoxy-2-pentenoyl chloride (15 mm) and THF (15 ml.), at 0°, is prepared and then slight excess of methylamine introduced. The reaction mixture is allowed to stand under nitrogen for about one hour. Then the reaction is allowed to rise to RT and solvent removed. The residue is taken up in methylene dichloride, washed, dried and solvent removed under vacuum to yield N-methyl 4-[4-(2-chloro-4-trifluoromethylphenoxy) phenoxy]-3-methoxy-2-pentenamide.

Workup

  1. customat 0°, is prepared
  2. customto rise to RT
  3. customsolvent removed
  4. washwashed
  5. customdried
  6. customsolvent removed under vacuum

Sources & evidence

ORD record
ord-c6a4d00b427246a2bf5c9758a1aa9042
Source dataset
uspto-grants-1983_10
Patent number
US04408076

Reaction notes

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