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Water → Methyl 3-(3,4-dinitrobenzyl)-2-oxo-2,3-dihydrobenzoxazole-5-carboxylate

HRID 655317
Notes
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Reaction equation

HRID 655317 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=[CH:10][C:4]=2[O:3]1.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([N+:26]([O-:28])=[O:27])[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[N+:26]([C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[N+:23]([O-:25])=[O:24])[CH2:16][N:6]1[C:5]2[CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=[CH:10][C:4]=2[O:3][C:2]1=[O:1])([O-:28])=[O:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12395109Methyl 2-oxo-2,3-dihydro-1,3-benzoxazole-5-carboxylateHCID 230095504-Bromomethyl-1,2-dinitrobenzene

Product 1

HCID 58486041Methyl 3-(3,4-dinitrobenzyl)-2-oxo-2,3-dihydrobenzoxazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
80 °C

Procedure

2 g (10.4 mmol) of methyl 2-oxo-2,3-dihydrobenzoxazole-5-carboxylate, 2.97 g (11.4 mmol) of 4-bromomethyl-1,2-dinitrobenzene (prepared in a corresponding manner to DE 3904797) and 5.7 g (41.4 mmol) of potassium carbonate are suspended in 50 ml of acetonitrile, and the mixture is stirred at 80° C. for 1 h. The reaction mixture is poured into 50 ml of water, extracted with 500 ml of MTBE, dried and evaporated to dryness. The residue is purified by column chromatography on silica gel; product: 1.5 g;

Workup

  1. extractionextracted with 500 ml of MTBE
  2. customdried
  3. customevaporated to dryness
  4. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-52534a58a00e4f0eb1e3ac5a4798258f
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08071593B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes