Triethylamine → N2-(4-bromophenyl)-7-isopropyl-1,3-benzoxazol-2-amine

HRID 2056132ノート

反応式

HRID 2056132 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([CH3:10])[CH3:9])[C:3]=1[OH:11].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]=[C:20]=S)=[CH:15][CH:14]=1.C(N(CC)CC)C.C(OCC)(=O)C>O1CCCC1.S([O-])([O-])(=O)=O.[Cu+2]>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[O:11][C:3]3[C:4]([CH:8]([CH3:9])[CH3:10])=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)=[CH:15][CH:14]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 161334-Bromophenyl isothiocyanateHCID 146849822-Amino-6-isopropylphenol

生成物 1

HCID 22347135N2-(4-bromophenyl)-7-isopropyl-1,3-benzoxazol-2-amine収率 91%

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 2-amino-6-isopropylphenol (0.354 g, 2.34 mmol) and 4-bromophenylisothiocyanate (0.500 g, 2.34 mmol) in tetrahydrofuran (35 mL) was stirred at room temperature for 3 h. Anhydrous copper (II) sulfate (3.361 g, 21.06 mmol), silica gel (3.361 g), and triethylamine (0.236 g, 0.33 mL, 2.34 mmol) were added, and the mixture stirred at room temperature for 18 h. The reaction mixture was filtered through a pad of Celite and the washed with diethyl ether (3×50 mL). The filtrate was concentrated to afford a brown solid. The solid material was applied to silica gel and passed through a pad a silica gel along with ethyl acetate (3×50 mL). The filtrate was concentrated to afford N2-(4-bromophenyl)-7-isopropyl-1,3-benzoxazol-2-amine (0.702 g, 91%). RP-HPLC Rt 18.066 min, 86% purity (5% to 85% acetonitrile/0.1M aqueous ammonium acetate, buffered to pH 4.5, over 20 min at 1 mL/min; λ=254 nm; Deltapak C18, 300 Å, 5 μm, 150×3.9 mm column); m/z 333 (MH+).

後処理

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washthe washed with diethyl ether (3×50 mL)
  3. concentrationThe filtrate was concentrated
  4. customto afford a brown solid
  5. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-53109500b82e437aacaa3798df839985
出典データセット
uspto-grants-2008_02
特許番号
US07332497B2

反応ノート

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