Water → HCID 18431474, compound

HRID 1278931Notes

Reaction equation

HRID 1278931 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-3b1ea46c441d4379969ce9f0777f4e31
Source dataset
uspto-grants-2002_09
Patent number
US06444812B1

Reaction notes

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