Water → HCID 18431474, compound

HRID 635262Notes

Reaction equation

HRID 635262 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:13][C:14]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:20]([Br:26])=[CH:19][C:15]=1[C:16](O)=[O:17].Cl.[CH3:28][O:29][NH:30][CH3:31].O>C(Cl)Cl>[NH2:13][C:14]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:20]([Br:26])=[CH:19][C:15]=1[C:16]([N:30]([O:29][CH3:28])[CH3:31])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 184314782-Amino-5-bromo-3-nitrobenzoic acid

Product 1

HCID 18431474HCID 18431474, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1′-Carbonyldiimidazole (41 g) was added portionwise at room temperature to a mixture of 2-amino-5-bromo-3-nitro-benzoic acid (55 g) in DCM (700 ml). The mixture was stirred at room temperature for 1 hour. N-methoxy-methanamine hydrochloride (24.6 g) was added. The mixture was stirred at room temperature overnight and hydrolized with water. The precipitate was filtered off and the filtrate was decanted. The organic layer was dried, filtered and the solvent was evaporated till dryness. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/ethyl acetate 98/2). The pure fractions were collected and the solvent was evaporated. The precipitate was taken up in HCl 3N (250 ml). The mixture was stirred at room temperature for 4 hours. The precipitate was filtered off, washed with water and dried, yielding 23 g of 2-amino-5-bromo-N-methoxy-N-methyl-3-nitrobenzamide (interm. 55, mp. 129° C.)

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe filtrate was decanted
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customthe solvent was evaporated till dryness
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/ethyl acetate 98/2)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated
  9. stirringThe mixture was stirred at room temperature for 4 hours
  10. filtrationThe precipitate was filtered off
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-9854a721e82346b39fb53187fefa8573
Source dataset
uspto-grants-2001_02
Patent number
US06187786B1

Reaction notes

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