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

HRID 1456278노트

반응식

HRID 1456278 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 methylenes 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.

후처리

  1. stirringthe mixture is stirred for 18 hours
  2. customThe tetrahydrofuran is evaporated in vacuo to a residue which
  3. customis partitioned between methylenes 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

출처 및 근거

ORD 기록
ord-203c3ae938f040b2abe8fefac3d8c22a
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05843952

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