2-Methylbenzyl alcohol → (2-Methylphenyl)methyl 4-[(6,11-dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl)benzoate

HRID 962595Notes

Reaction equation

HRID 962595 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[H-].[Na+].[CH:12]1[C:22]2[CH2:21][C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[CH2:18][N:17]([C:27]([C:29]3[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=3)=[O:28])[C:16]=2[CH:15]=[CH:14][CH:13]=1>O1CCCC1>[CH:12]1[C:22]2[CH2:21][C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[CH2:18][N:17]([C:27]([C:29]3[CH:30]=[CH:31][C:32]([C:33]([O:5][CH2:4][C:3]4[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=4[CH3:1])=[O:34])=[CH:36][CH:37]=3)=[O:28])[C:16]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 69942-Methylbenzyl alcoholHCID 24758Sodium hydrideHCID 538022444-[(6,11-dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]benzoyl chloride

Product 1

HCID 86751575(2-Methylphenyl)methyl 4-[(6,11-dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl)benzoateYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 248 mg of 2-methylbenzyl alcohol in 4 ml of anhydrous tetrahydrofuran is added 80 mg of sodium hydride (60% in mineral oil) and the mixture stirred for 1 hour. To the mixture is added 430 mg of 4-[(6,11-dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]benzoyl chloride and the mixture is stirred for 18 hours. The tetrahydrofuran is evaporated in vacuo to a residue which is partitioned between methylene chloride and water. The organic layer is separated and washed with 1N HCl, water, 1M NaHCO3, and brine. The organic layer is dried (Na2SO4) and passed through a short pad of hydrous magnesium silicate and hexane added at the boil to give 170 mg of the desired product, m.p. 140°-142° C.

Workup

  1. stirringthe mixture is stirred for 18 hours
  2. customThe tetrahydrofuran is evaporated in vacuo to a residue which
  3. customis partitioned between methylene chloride and water
  4. customThe organic layer is separated
  5. washwashed with 1N HCl, water, 1M NaHCO3, and brine
  6. dry with materialThe organic layer is dried (Na2SO4)
  7. additionadded at the boil

Sources & evidence

ORD record
ord-27ed193435b6444a87ff93f1d306dffe
Source dataset
uspto-grants-1998_06
Patent number
US05760031

Reaction notes

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