Hydrochloric Acid → N-(t-butoxy)-5-(4-chlorophenyl)4-(2,4-dichlorophenyl)thiazole-2-carboxamide

HRID 1392363ノート

反応式

HRID 1392363 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=O)=[N:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[C:57]([O:61][NH2:62])([CH3:60])([CH3:59])[CH3:58].Cl>C(#N)C.C(OCC)(=O)C>[C:57]([O:61][NH:62][C:13]([C:11]1[S:12][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:9]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[N:10]=1)=[O:15])([CH3:60])([CH3:59])[CH3:58]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2777907O-tert-butylhydroxylamineHCID 10045599HCID 10045599、化合物

生成物 1

HCID 86595683N-(t-butoxy)-5-(4-chlorophenyl)4-(2,4-dichlorophenyl)thiazole-2-carboxamide収率 51%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Part B; 5-(4-Chlorophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxylic acid (1.00 gram, 2.6 mmol) is suspended in anhydrous acetonitrile (20 mL) under a nitrogen atmosphere at room temperature. Diisopropylethylamine (DIPEA) (1.36 mL, 7.8 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU) (1.08 gram, 2.85 mmol) and O-tert-butylhydroxylamine.HCl (0.35 gram, 25.1 mmol) are successively added and the resulting mixture is stirred overnight at room temperature. The resulting mixture is concentrated in vacuo and dichloromethane is added. The resulting solution is successively washed with water and brine, dried over MgSO4, filtered and evaporated in vacuo. Subsequent flash chromatography (ethyl acetate:petroleum ether (40-60)=1:3 (v/v)) gives N-(t-butoxy)-5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxamide (0.60 gram, 51% yield) as a white foam. 1H-NMR (400 MHz, CDCl3): δ 9.20 (s, 1H), 7.47 (t, J=2 Hz, 1H), 7.25-7. (m, 4H), 7.14 (dt, J=8 Hz, J=2 Hz, 2H), 1.36 (s, 9H).

後処理

  1. concentrationThe resulting mixture is concentrated in vacuo and dichloromethane
  2. additionis added
  3. washThe resulting solution is successively washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-ad8f21a2cfca437da949bc55155f3dc5
出典データセット
uspto-grants-2008_03
特許番号
US07342032B2

反応ノート

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