N,N-Dimethylaniline → HCID 68686100, compound

HRID 2244260Notes

Reaction equation

HRID 2244260 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][N:14]3[CH:22]=[CH:23][CH:24]=[C:13]3[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CN(C)C1C=CC=CC=1.[Cl:34][C:35]([Cl:40])([Cl:39])[C:36](Cl)=[O:37]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][N:14]3[C:22]([C:36](=[O:37])[C:35]([Cl:40])([Cl:39])[Cl:34])=[CH:23][CH:24]=[C:13]3[CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 6420Trichloroacetyl chlorideHCID 6868787110-[(4-Bromophenyl)sulfonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 68686100HCID 68686100, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10-[(4-bromophenyl)sulfonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine of Step A (2.32 g, 5.753 mmol) and N,N-dimethylaniline (1.17 mL, 9.204 mmol) in dry dichloromethane (20 mL) at 0° C. under nitrogen was added dropwise trichloroacetyl chloride (0.96 mL, 8.629 mmol). The ice bath was removed and the reaction mixture stirred at room temperature for 21 hours. The reaction mixture was then washed with 2 M hydrochloric acid (2×100 mL) and water (100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give an olive foam. Purification by flash chromatography using a solvent gradient of 5-15% ethyl acetate in hexane afforded a cream solid that was recrystallized from diethyl ether/hexane to afford the title compound (1.986 g, 63%) as an off-white crystalline solid, m.p. 182-183 ° C.

Workup

  1. customThe ice bath was removed
  2. washThe reaction mixture was then washed with 2 M hydrochloric acid (2×100 mL) and water (100 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give an olive foam
  6. customPurification by flash chromatography
  7. customafforded a cream solid
  8. customthat was recrystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-e686264d6c1542fb9c8a4be9bca9c280
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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