3-Chloroaniline → 4-(3-Chloro-phenylamino)-1,1,1-trifluoro-4-phenyl-but-3-en-2-one

HRID 1163246Notes

Reaction equation

HRID 1163246 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3](=[O:12])[C:4]#[C:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19]>CO>[Cl:15][C:16]1[CH:17]=[C:18]([NH:19][C:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH:4][C:3](=[O:12])[C:2]([F:13])([F:14])[F:1])[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 111272271,1,1-Trifluoro-4-phenyl-but-3-yn-2-one

Product 1

HCID 666768124-(3-Chloro-phenylamino)-1,1,1-trifluoro-4-phenyl-but-3-en-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 1-Neck round-bottom flask was added 1,1,1-trifluoro-4-phenyl-but-3-yn-2-one (2.0 g, 0.01 mole), methanol (5 mL) and m-chloroaniline (0.961 mL, 0.0091 mol). The reaction was stirred. TLC (SiO2, hexanes/methylene chloride 1:1) indicated near reaction completion after 1 h. After 1.5 h the product was concentrated in vacuo to afford an orange oil, which was placed on high vacuum overnight, affording a yellow gum. The crude product was chromatographed on Silica gel with hexanes, Methylene Chloride 2:1, and place on high vacuum for 2 h to afford the title compound as a yellow gum; 1H NMR (CDCl3, 400 MHz) δ 5.74 (s, 1H), 6.67-6.69 (m, 1H), 6.85 (m, 1H), 7.08-7.10 (m, 1H), 7.31-7.39 (m, 4H), 7.43-7.47 (tt, 1H), 12.39 (bs, 1H)

Workup

  1. concentrationAfter 1.5 h the product was concentrated in vacuo
  2. customto afford an orange oil, which
  3. customwas placed on high vacuum overnight
  4. customaffording a yellow gum
  5. customThe crude product was chromatographed on Silica gel with hexanes, Methylene Chloride 2:1, and place on high vacuum for 2 h

Sources & evidence

ORD record
ord-0c24e556dbe2477495fc1a413c1a9ae2
Source dataset
uspto-grants-2010_10
Patent number
US07820662B2

Reaction notes

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