Aniline → Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-phenylamino-2-pentenoate

HRID 1980347Notes

Reaction equation

HRID 1980347 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:26]=[CH:25][C:6]([O:7][C:8]2[CH:24]=[CH:23][C:11]([O:12][CH:13]([CH3:22])[C:14](=O)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1C=CC=CC=1>[F:1][C:2]([F:27])([F:28])[C:3]1[CH:26]=[CH:25][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]([O:12][CH:13]([CH3:22])[C:14]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:23][CH:24]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 13469151Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-oxopentanoate

Product 1

HCID 70489003Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-phenylamino-2-pentenoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Using the procedure of Reynolds and Hauser, Org. Syn. Coll. Vol 3, a mixture of ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-oxopentanoate (1.51 g), benzene (15 ml) and aniline (0.5 g) is azeotropically distilled. The reaction product is purified using a florisil column and eluting with hexane/ethylacetate (9:1) to yield (fractions 2, 3 and 4) ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-phenylamino-2-pentenoate.

Workup

  1. distillationis azeotropically distilled
  2. customThe reaction product is purified
  3. washeluting with hexane/ethylacetate (9:1)

Sources & evidence

ORD record
ord-9aad0bcfdac54a00bd3a288cc18349e7
Source dataset
uspto-grants-1985_04
Patent number
US04508906

Reaction notes

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