Water → HCID 14535965, compound

HRID 2372433Notes

Reaction equation

HRID 2372433 reaction equation
CO[C:3](=[O:18])[CH2:4][CH2:5][C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=[N:8][CH:7]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([Mg]Br)=[CH:22][CH:21]=1.O>O1CCCC1>[CH2:11]([N:10]1[C:6]([CH2:5][CH2:4][C:3]([C:23]2[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=2)([C:23]2[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=2)[OH:18])=[CH:7][N:8]=[CH:9]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14535954HCID 14535954, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 14535965HCID 14535965, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-benzyl-5-imidazole propionic acid methyl ester (6,4 g) in tetrahydrofuran is heated at 60° C. and to this is then added dropwise p-chlorophenylmagnesium bromide prepared above. After the addition is complete, the reaction mixture is refluxed for an additional 3 hours, cooled and poured into cold water. Tetrahydrofuran is evaporated, toluene is added and the mixture is made acidic with hydrochloric acid. The precipitated product is filtered, washed with ether and dried. Yield 12,2 g; m.p. 210°-213° C. M.p. of nitrate 157°-160° C. (made in water-ether mixture). M.p. of hydrochloride (from ethylacetate) 178°-187° C.

Workup

  1. customprepared above
  2. additionAfter the addition
  3. temperaturethe reaction mixture is refluxed for an additional 3 hours
  4. temperaturecooled
  5. customTetrahydrofuran is evaporated
  6. additiontoluene is added
  7. filtrationThe precipitated product is filtered
  8. washwashed with ether
  9. customdried
  10. customM.p. of nitrate 157°-160° C. (made in water-ether mixture)
  11. customM.p. of hydrochloride (from ethylacetate) 178°-187° C.

Sources & evidence

ORD record
ord-b2ab9d71ab6042b7965308f30c5163dd
Source dataset
uspto-grants-1992_03
Patent number
US05098923

Reaction notes

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