Water → HCID 19904240, compound

HRID 2372435Notes

Reaction equation

HRID 2372435 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]([CH3:10])[CH:6]=[C:7]([CH3:9])[CH:8]=1.C(O[C:14](=[O:29])[CH2:15][CH2:16][C:17]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:20]=[N:19][CH:18]=1)C.O>O1CCCC1>[CH2:22]([N:21]1[C:17]([CH2:16][CH2:15][C:14]([C:3]2[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[CH:4]=2)([C:3]2[CH:4]=[C:5]([CH3:10])[CH:6]=[C:7]([CH3:9])[CH:8]=2)[OH:29])=[CH:18][N:19]=[CH:20]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 136357Benzene, 1-bromo-3,5-dimethyl-HCID 5462224MagnesiumHCID 53786379HCID 53786379, compound

Product 1

HCID 19904240HCID 19904240, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

1,06 g of magnesium turnings are covered with 30 ml of dry tetrahydrofuran. To the mixture is then added dropwise a solution of 5-bromo-m-xylene (8,14 g) in 10 ml of dry tetrahydrofuran at such a rate that a smooth reaction is maintained. After the addition is complete, the reaction mixture is refluxed for one additional hour and cooled to room temperature. The reaction mixture is then added dropwise to a solution of 1-benzyl-5-imidazole propionic acid ethyl ester (5,0 g) in 40 ml of tetrahydrofuran at 60° C. After the addition is complete, the reaction mixture is refluxed for 2 hours, cooled and poured into cold water. Tetrahydrofuran is evaporated and to the solution is added conc. hydrochloric acid. The solution is cooled, some ether is added and the precipitate which contains the product as hydrochloride salt is removed by filtration, washed and dried. Yield 4,1 g. M.p. 120°-124° C.

Workup

  1. customthat a smooth reaction
  2. temperatureis maintained
  3. additionAfter the addition
  4. temperaturethe reaction mixture is refluxed for one additional hour
  5. additionAfter the addition
  6. temperaturethe reaction mixture is refluxed for 2 hours
  7. temperaturecooled
  8. customTetrahydrofuran is evaporated and to the solution
  9. additionis added conc. hydrochloric acid
  10. temperatureThe solution is cooled
  11. additionsome ether is added
  12. customis removed by filtration
  13. washwashed
  14. customdried

Sources & evidence

ORD record
ord-28f0ac5850a74a218dcab841a8b09cf4
Source dataset
uspto-grants-1992_03
Patent number
US05098923

Reaction notes

Loading…