Hydrochloric Acid → HCID 86626060, compound

HRID 2239517Notes

Reaction equation

HRID 2239517 reaction equation
[N:1]([O-])=O.[Na+].[Br:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][C:7]=1[O:13][CH3:14].Cl.[C:16]([CH2:18][C:19]([NH2:21])=[O:20])#[N:17].O.O.O.C([O-])(=O)C.[Na+]>O.C(O)C>[Br:5][C:6]1[CH:12]=[CH:11][C:9]([N:10]=[N:1][CH:18]([C:16]#[N:17])[C:19]([NH2:21])=[O:20])=[CH:8][C:7]=1[O:13][CH3:14]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7898CyanoacetamideHCID 70182544-Bromo-3-methoxyanilineHCID 23665404Sodium Acetate TrihydrateHCID 23668193Sodium Nitrite

Product 1

HCID 86626060HCID 86626060, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Procedure

Sodium nitrite (8.54 g, 123.7 mmol) dissolved in water (100 ml) was added to an ice-cold suspension of 4-bromo-3-methoxyaniline (25 g, 123.7 mmol) in concentrated HCl (46 ml, 1514 mmol) and water (100 ml). After stirring for 10 minutes, 2-cyanoacetamide (10.40 g, 123.7 mmol) and sodium acetate trihydrate (84 g, 617 mmol) in water (1.8 L) was added and the reaction was allowed to stir overnight. The resulting solid was collected by filtration, washed with water, dried, giving an orange solid which was refluxed in 1.4 L of ethanol for 30 min. The mixture was cooled to room temperature, the solid was collected by filtration, washed with ethanol (100 ml×3), and dried to yield the title compound as a yellow solid (34.4 g, 94%). 1H NMR: 11.70 (s, 1H), 7.90 (s, 1H), 7.50 (m, 2H), 7.35 (s, 1H), 7.20 (d, 1H), 3.90 (s, 3H); m/z: 296.

Workup

  1. stirringto stir overnight
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried
  5. customgiving an orange solid which
  6. filtrationthe solid was collected by filtration
  7. washwashed with ethanol (100 ml×3)
  8. customdried

Sources & evidence

ORD record
ord-c70e9028d96e4d48be1ac8329c211fae
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

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