Trichloroacetyl chloride → 2,2,2-Trichloro-1-[10-(9H-fluorene-2-carbonyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]-ethanone

HRID 2244298Notes

Reaction equation

HRID 2244298 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[C:14]([N:16]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH2:20][N:19]2[CH:27]=[CH:28][CH:29]=[C:18]2[CH2:17]1)=[O:15].[Cl:30][C:31]([Cl:36])([Cl:35])[C:32](Cl)=[O:33]>O1CCOCC1>[Cl:30][C:31]([Cl:36])([Cl:35])[C:32]([C:27]1[N:19]2[C:18]([CH2:17][N:16]([C:14]([C:2]3[CH:3]=[CH:4][C:5]4[C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[CH2:12][C:13]=4[CH:1]=3)=[O:15])[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20]2)=[CH:29][CH:28]=1)=[O:33]

Participants

4

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 6869069310-(9H-Fluoren-2-ylcarbonyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 686864232,2,2-Trichloro-1-[10-(9H-fluorene-2-carbonyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]-ethanoneYield 88.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 25 mL of 1,4-dioxane was added 0.59 g (0.0016 mol) of 10-(9H-fluoren-2-ylcarbonyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine opf Step A followed by the addition of 0.31 g (0.0017 mol) of trichloroacetyl chloride. The solution was heated under reflux for 10 minutes, cooled to room temperature and poured into ice water with stirring The precipitate was collected, washed with water and dried yielding 0.74 g of title compound which was used directly in the next step.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 10 minutes
  3. customwas collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-8a607f0b468f42d086b8e5b8b9bbd66c
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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