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

HRID 491423노트

반응식

HRID 491423 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fc34251dfd6942bca4cfe19f6292bf63
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531542B2

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