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

HRID 371022Notes

Reaction equation

HRID 371022 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-e9b0ee8bcf4c49cc861d9fb109c72c90
Source dataset
uspto-grants-1985_07
Patent number
US04529438

Reaction notes

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