Imidazole → {4-Chloro-2-[alpha-(1-imidazolyl)-benzyl]-phenyl}-(2,4-dichlorobenzyl)-ether

HRID 435881Notes

Reaction equation

HRID 435881 reaction equation
ClC1C=CC(O)=C(C=1)C(C1C=CC=CC=1)=O.[BH4-].[Na+].N1C=CN=C1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([CH:32]([N:39]2[CH:43]=[CH:42][N:41]=[CH:40]2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:26]=1.[H-].[Na+].[Cl:46][C:47]1[CH:54]=[C:53]([Cl:55])[CH:52]=[CH:51][C:48]=1[CH2:49]Cl>CO.C(O)C.CN(C)C=O.O.C1C=CC=CC=1>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:49][C:48]2[CH:51]=[CH:52][C:53]([Cl:55])=[CH:54][C:47]=2[Cl:46])=[C:27]([CH:32]([N:39]2[CH:43]=[CH:42][N:41]=[CH:40]2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:26]=1

Participants

12

Reactant 6

HCID 795ImidazoleHCID 6799Chlorohydroxy benzophenoneHCID 72122,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 4311764Sodium borohydrideHCID 125771204-Chloro-2-[(1H-imidazol-1-yl)(phenyl)methyl]phenol

Product 1

HCID 21481666{4-Chloro-2-[alpha-(1-imidazolyl)-benzyl]-phenyl}-(2,4-dichlorobenzyl)-ether

Reagents, catalysts & solvents 5

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

23 g. of 5-chloro-2-hydroxybenzophenone is reduced with an excess of sodium borohydride in methanol, thus obtaining 10.5 g. of 5-chloro-2-hydroxybenzohydrol, m.p. 132°-134° (from benzene). 2.3 g. of this product is heated with 670 mg. of imidazole for 2.5 hours to 200°. The reaction mixture is then dissolved in ethanol, a small amount of water is added, and this yields 500 mg. of 4-chloro-2-[α-(1-imidazolyl)-benzyl]-phenol, m.p. 228°-232°. The product is stirred in 7.5 ml. of dimethylformamide with 65 mg. of sodium hydride suspension (80%) for 1.5 hours at room temperature and then combined with 440 mg. of 2,4-dichlorobenzyl chloride. After the mixture has been worked up as set forth in Example 1, it is recrystallized from benzene/cyclohexane, thus obtaining 430 mg. of {4-chloro-2-[α-(1-imidazolyl)-benzyl[-phenyl}-(2,4-dichlorobenzyl)-ether, m.p. 115°-120°.

Workup

  1. customthus obtaining 10.5 g
  2. temperatureof this product is heated with 670 mg
  3. customis recrystallized from benzene/cyclohexane
  4. customthus obtaining 430 mg

Sources & evidence

ORD record
ord-289b7c0bf4e441c5bc0032311e58ccba
Source dataset
uspto-grants-1977_02
Patent number
US04006243

Reaction notes

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