Dichloromethane → 2-(4-Tert-butylphenyl)-7-nitro-1,3-benzooxazole

HRID 491423ノート

反応式

HRID 491423 の反応式
[C:1]([C:5]1[CH:23]=[CH:22][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:13]=2[OH:21])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(Cl)Cl>O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]2[O:21][C:13]3[C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=2)=[CH:22][CH:23]=1)([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 576783014-tert-butyl-N-(2-hydroxy-3-nitrophenyl)benzamide

生成物 1

HCID 576783112-(4-Tert-butylphenyl)-7-nitro-1,3-benzooxazole収率 79%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 4-tert-butyl-N-(2-hydroxy-3-nitrophenyl)benzamide (0.35 g, 1.11 mmol) and pyridinium p-toluenesulfonate (200 mg, 0.8 mmol) in xylenes (25 mL) was heated in a 135° C. bath for 72 h. The solution was cooled to room temperature, and CH2Cl2 (100 mL) and H2O (25 mL) were added. The layers were separated, and the aqueous layer was extracted with CH2Cl2 (50 mL). The combined organic layers were washed with brine (25 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to afford the title compound (0.260 g) as a golden solid. MS (ESI-POS): [M+H]+=297; Anal. Calcd for C17H16N2O3: C, 68.91; H, 5.44; N, 9.45. Found: C, 69.02; H, 5.43; N, 9.00.

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (50 mL)
  3. washThe combined organic layers were washed with brine (25 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-fc34251dfd6942bca4cfe19f6292bf63
出典データセット
uspto-grants-2009_05
特許番号
US07531542B2

反応ノート

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