Water → HCID 178488937, compound

HRID 235957Notes

Reaction equation

HRID 235957 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.O.C([O-])([O-])=O.[Na+].[Na+]>CC#N>[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 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 178488953HCID 178488953, compound

Product 1

HCID 178488937HCID 178488937, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 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-4dae3573cbad42f4bb01b1d41ec205fd
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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