Hydrochloric Acid → HCID 86592822, compound

HRID 857156Notes

Reaction equation

HRID 857156 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([N+:20]([O-])=O)[CH:14]=2)=[C:7]([Br:23])[CH:6]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].Br[C:34]1C=C(CC(OC)=O)C=C(Br)[C:39]=1OC1C=CC(N)=C(N)C=1.Cl.C(CC(=O)C)(=O)C>CO>[Br:23][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:24])[CH:10]=[C:9]([Br:11])[C:8]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]2[N:19]=[C:34]([CH3:39])[NH:20][C:15]=2[CH:14]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24489Sodium DithioniteHCID 31261AcetylacetoneHCID 21867239HCID 21867239, compoundHCID 86592823HCID 86592823, compound

Product 1

HCID 86592822HCID 86592822, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl[3,5-dibromo-4-(4-amino-3-nitrophenoxy)phenyl]acetate (1.1 g, Example 2(b)) was treated with sodium dithionite as described in Example 2(c). The formed methyl [3,5-dibromo-4-(3,4-diaminophenoxy)phenyl]acetate was dissolved in methanol (36 mL). An aqueous solution of hydrochloric acid (35%, 2.1 mL) was added, followed by acetylacetone (0.48 g). The reaction mixture was refluxed for 5.5 hours, cooled down and the formed yellow precipitate was filtered off. After recrystallisation from ethanol, 80 mg (5%) of methyl [3,5-dibromo-4-(2-methyl-5-benzoimidazolyloxy)phenyl]acetate was obtained.

Workup

  1. temperatureThe reaction mixture was refluxed for 5.5 hours
  2. temperaturecooled down
  3. filtrationthe formed yellow precipitate was filtered off
  4. customAfter recrystallisation from ethanol

Sources & evidence

ORD record
ord-b456b09656f942929e2a6c8e17056ccd
Source dataset
uspto-grants-2006_12
Patent number
US07144909B2

Reaction notes

Loading…