Sodium Carbonate → HCID 178488937, compound

HRID 1722007Notes

Reaction equation

HRID 1722007 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[CH:5][CH:4]=1.C1C=C[NH+]=CC=1.[Br:21][Br-]Br.C([O-])([O-])=O.[Na+].[Na+]>CC#N.O>[Br:21][C:11]1[NH:10][C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[N:13][C:12]=1[CH3:14]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 178488953HCID 178488953, compound

Product 1

HCID 178488937HCID 178488937, compoundYield 37.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent3×

Procedure

2-(p-Methoxyphenyl)-4-methylimidazole, (5.0 g, 0.0265 mole), was dissolved in CH3CN (250 ml) at the boiling point. The solution was cooled to room temperature and stirred while a solution of pyridinium bromide perbromide (7.0 g) in CH3CN (70 ml) was added dropwise. A precipitate separated as the addition was completed (30 min) and stirring was continued for 30 minutes. The mixture was poured into water (1.5 L) and the precipitated hydrobromide salt was collected. The filtrate was made basic with saturated Na2CO3 solution and the product was collected, washed with water, and dried to afford 2.45 g, m.p. 183°-187° C. The hydrobromide salt was dissolved in hot CH3CN (75 ml)-H2O (25 ml) and the solution was made basic with saturated Na2CO3 solution. A second crop of product was collected, washed with water, and dried to yield 2.2 g of 35; m.p. 179°-184° C.; 65 % combined yield. A sample of the first crop recrystallized from 50% CH3CN melted at 184°-187° C.

Workup

  1. additionwas added dropwise
  2. customA precipitate separated as the addition
  3. custom(30 min)
  4. additionThe mixture was poured into water (1.5 L)
  5. customthe precipitated hydrobromide salt was collected
  6. customthe product was collected
  7. washwashed with water
  8. customdried
  9. customto afford 2.45 g, m.p. 183°-187° C
  10. customA second crop of product was collected
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-5e7f3a2b1ad0402497d0e6b9fed6a07d
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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