N,O-Dimethylhydroxylamine → 2-Oxo-1-phenyl-2,3-dihydro-1H-benzoimidazole-5-carboxylic Acid Methoxy-methyl-amide

HRID 1828168Notes

Reaction equation

HRID 1828168 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=O.[N+](C1C=C(C=CC=1NC1C=CC=CC=1)[C:24](O)=[O:25])([O-])=O.C(C1NC=CN=1)(C1NC=CN=1)=O.[CH3:49][NH:50][O:51][CH3:52]>C1COCC1>[CH3:52][O:51][N:50]([CH3:49])[C:5]([C:4]1[CH:8]=[CH:9][C:10]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:24](=[O:25])[NH:1][C:2]=2[CH:3]=1)=[O:7]

Participants

6

Reactant 4

HCID 14232N,O-DimethylhydroxylamineHCID 7738213-Amino-4-phenylamino-benzoic acidHCID 38243664-Anilino-3-nitrobenzoic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 865879852-Oxo-1-phenyl-2,3-dihydro-1H-benzoimidazole-5-carboxylic Acid Methoxy-methyl-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-amino-4-phenylamino-benzoic acid (prepared from 3-nitro-4-phenylamino-benzoic acid as described in the general procedure, 2.04 gm, 8.94 mmol) in THF (25 mL) was added carbonyl diimidazole (3.62 gm, 22.34 mmol). After stirring for 1 hour at room temperature, N,O-dimethylhydroxyl amine (1.31 gm, 13.41 mmol) was added in one portion. Stirring was continued at room temperature for an additional 2 hours after which time the reaction was determined to be complete by LC-MS. The THF was removed in vacuo and the residue was diluted with water and extracted with methylene chloride three times. The combined methylene chloride extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2.23 gm of the title compound as a tan solid which was used without further purification.

Workup

  1. stirringStirring
  2. waitwas continued at room temperature for an additional 2 hours
  3. customThe THF was removed in vacuo
  4. additionthe residue was diluted with water
  5. extractionextracted with methylene chloride three times
  6. dry with materialThe combined methylene chloride extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-700ef45fd088435ebd1e9349334f1ba8
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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