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

HRID 491423Notes

Reaction equation

HRID 491423 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fc34251dfd6942bca4cfe19f6292bf63
Source dataset
uspto-grants-2009_05
Patent number
US07531542B2

Reaction notes

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