1,1'-Carbonyldiimidazole → HCID 10220713, compound

HRID 844114Notes

Reaction equation

HRID 844114 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)=[CH:4][C:3]=1[OH:17].[C:18](N1C=CN=C1)(N1C=CN=C1)=[O:19]>C1COCC1>[N+:14]([C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]3[NH:1][C:18](=[O:19])[O:17][C:3]=3[CH:4]=2)[CH:13]=[CH:12][CH:11]=1)([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 9794589HCID 9794589, compound

Product 1

HCID 10220713HCID 10220713, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-amino-3′-nitro-biphenyl-3-ol (0.115 g, 0.5 mmol) in dry THF (2.5 mL) was treated with a solution of 1,1′-carbonyldiimidazole (0.098 g, 0.6 mmol) in dry THF (2.5 mL). The reaction mixture was stirred at room temperature under a blanket of nitrogen for 6 hours. A precipitate formed, was collected and washed with methylene chloride (50 mL) to give 6-(3-nitro-phenyl)-3H-benzooxazol-2-one (0.095 g, 74%) as a white solid: mp 280-281° C.; 1H-NMR (DMSO-d6) δ11.7 (s, 1H), 8.43 (t, 1H, J=1.15 Hz), 8.2-8.13 (m, 2H), 7.79-7.72 (m, 2H), 7.59 (dd, 1H, J=8.08, 2.31 Hz), 7.21 (d, 1H, J=8.08 Hz), MS (ES) m/z 255([M−H]−, 100%); Anal. Calc. For C13H8N2O4: C, 60.94; H, 3.15; N, 10.93. Found: C, 59.95; H, 3.17; N, 10.77.

Workup

  1. customA precipitate formed
  2. customwas collected
  3. washwashed with methylene chloride (50 mL)

Sources & evidence

ORD record
ord-bd2bef0ecf2b4f81a4bef460dfd9ca1a
Source dataset
uspto-grants-2002_04
Patent number
US06380235B1

Reaction notes

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