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

HRID 2296536Notes

Reaction equation

HRID 2296536 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-4709881015664b8b87ca3ca33a234ade
Source dataset
uspto-grants-1984_01
Patent number
US04429167

Reaction notes

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