Sodium Hydroxide → 2-Amino-N-1H-imidazol-2-yl-3-nitrobenzamide

HRID 1844955Notes

Reaction equation

HRID 1844955 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.S(O)(O)(=O)=O.[NH2:52][C:53]1[NH:54][CH:55]=[CH:56][N:57]=1.[OH-].[Na+]>CN(C=O)C.[Cl-].[Na+].O>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:52][C:53]1[NH:54][CH:55]=[CH:56][N:57]=1)=[O:6]

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 2196332-Amino-3-nitrobenzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 669404372-Amino-N-1H-imidazol-2-yl-3-nitrobenzamideYield 78.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
75 °C

Procedure

5.0 g (27.4 mmol) of 2-amino-3-nitro-benzoic acid, 12.48 g (32.9 mmol) of HBTU were suspended in 20 mL of DMF. To this suspension, 10 mL of DIEA was added, and the resulting mixture was stirred for 10 minutes to form a paste. To this paste, 10 mL of DMF was added followed by 9 g (68.2 mmol) of 2-amino imidazole sulfate. The resulting mixture was heated at 75° C. for 3.0 h. The reaction mixture was cooled to room temperature and 5 mL of 2N NaOH was added followed by 200 mL of brine solution. A solid precipitated from the solution and was collected by filtration, washed with water (300 ml), ethyl acetate (100 ml), and dried under vacuum to provide 5.3 g (75%) of 2-amino-N-(1H-imidazol-2-yl)-3-nitro-benzamide as a yellow solid. The product was hydrogenated according to the general procedure C to give 2,3-diamino-N-(1H-imidazol-2-yl)-benzamide (4.5 g).

Workup

  1. customto form a paste
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customA solid precipitated from the solution
  4. filtrationwas collected by filtration
  5. washwashed with water (300 ml), ethyl acetate (100 ml)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-afc79636275b4985930f56f78d2f0025
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

Loading…