Sodium hydride → HCID 131723753, compound

HRID 1057499Notes

Reaction equation

HRID 1057499 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]1[NH:10][CH:11]=[C:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[N:13]=1.[H-].[Na+].Br[CH2:27]/[CH:28]=[CH:29]/[C:30]([O:32][CH3:33])=[O:31]>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]1[NH:10][C:11]([CH2:27]/[CH:28]=[CH:29]/[C:30]([O:32][CH3:33])=[O:31])=[C:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[N:13]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 53691752-Butenoic acid, 4-bromo-, methyl esterHCID 178525048HCID 178525048, compound

Product 1

HCID 131723753HCID 131723753, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of phenylmethyl 2-[(2-bromophenyl)methyl]imidazole-4-carboxylate in dimethyl foramide (0.1M) was added sodium hydride (1.2 eq) The reaction was allowed to stir for 10 mins. followed by addition of methyl 4-bromocrotonate continued stirring for 18 hr. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was extracted with 10% hydrochloric acid and the aqueous layer was neutralized with saturated sodium carbonate. The aqueous layer eas extracted with ethyl acetate and dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (50% EtOAc/Hexane). EI-MS m/z 406/408 (M+H)+

Workup

  1. stirringcontinued stirring for 18 hr
  2. extractionextracted with ethyl acetate
  3. extractionThe organic layer was extracted with 10% hydrochloric acid
  4. extractionThe aqueous layer eas extracted with ethyl acetate
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (50% EtOAc/Hexane)

Sources & evidence

ORD record
ord-8ffb09ba70d64803aa001396d00a603f
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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