Trichloroacetyl chloride → HCID 18449079, compound

HRID 1270184Notes

Reaction equation

HRID 1270184 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.[Cl:29][C:30]([Cl:35])([Cl:34])[C:31](Cl)=[O:32]>ClCCl>[Cl:29][C:30]([Cl:35])([Cl:34])[C:31]([C:24]1[N:16]2[C:15]([CH2:14][N:13]([C:11](=[O:12])[C:10]3[CH:27]=[CH:28][C:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:8][CH:9]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17]2)=[CH:26][CH:25]=1)=[O:32]

Participants

4

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 10177192HCID 10177192, compound

Product 1

HCID 18449079HCID 18449079, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10-(4-cyclohexylbenzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine of Example 4 (1.85 g) in dichloromethane (50 mL) was added trichloroacetyl chloride (1 g). After stirring overnight at room temperature, the mixture was 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 eluate was combined and refluxed with gradual addition of hexane until crystallization was observed. The title compound (1.5 g) was obtained upon cooling, as colorless crystals, m.p. 172–174° C.

Workup

  1. washthe mixture was washed with saturated aqueous sodium bicarbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered through a short column of Magnesol®
  4. washAfter eluting with several additional volumes of dichloromethane
  5. temperaturerefluxed with gradual addition of hexane until crystallization

Sources & evidence

ORD record
ord-df3ed1b48ffb43969cdb21ab34a8115a
Source dataset
uspto-grants-2007_04
Patent number
US07202239B2

Reaction notes

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