O-Xylene → HCID 10280053, compound

HRID 1270181Notes

Reaction equation

HRID 1270181 reaction equation
[CH:1]1([C:7]2[CH:28]=[CH:27][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][N:16]4[CH:24]=[CH:25][CH:26]=[C:15]4[CH2:14]3)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C)C(C)=CC=CC=1.[C:37]([C:41]1[CH:49]=[CH:48][C:44]([C:45](Cl)=[O:46])=[CH:43][CH:42]=1)([CH3:40])([CH3:39])[CH3:38]>O>[C:37]([C:41]1[CH:42]=[CH:43][C:44]([C:45]([C:24]2[N:16]3[C:15]([CH2:14][N:13]([C:11](=[O:12])[C:10]4[CH:27]=[CH:28][C:7]([CH:1]5[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]5)=[CH:8][CH:9]=4)[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17]3)=[CH:26][CH:25]=2)=[O:46])=[CH:48][CH:49]=1)([CH3:40])([CH3:38])[CH3:39]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 743724-tert-Butylbenzoyl chlorideHCID 10177192HCID 10177192, compound

Product 1

HCID 10280053HCID 10280053, compoundYield 6.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10-(4-cyclohexyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine of Example 4 (1.85 g), dry xylene (25 mL) and 4-tert-butylbenzoylchloride (1.97 g) was refluxed overnight. The reaction mixture was poured into water, washed with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate and filtered through a short column of Magnesol®. After eluting with several additional volumes of dichloromethane, the combined eluate was refluxed with the gradual addition of hexane until crystallization was noted. Cooling and trituration provided the desired title product (0.18 g) as off-white crystals, m.p. 143–145° C.

Workup

  1. temperaturewas refluxed overnight
  2. washwashed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered through a short column of Magnesol®
  5. washAfter eluting with several additional volumes of dichloromethane
  6. temperaturethe combined eluate was refluxed with the gradual addition of hexane until crystallization
  7. temperatureCooling

Sources & evidence

ORD record
ord-536459f100fe465fa18ad35a9d3d2a12
Source dataset
uspto-grants-2007_04
Patent number
US07202239B2

Reaction notes

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