Sodium hydride → HCID 68857423, compound

HRID 1370797Notes

Reaction equation

HRID 1370797 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:7]=1[CH3:15].[H-].[Na+].[CH2:31](Br)[CH:32]=[CH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C=O)C.C(OCC)C>[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:31][CH:32]=[CH:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:19][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:7]=1[CH3:15]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 98116BromomethylstyreneHCID 18512160N-(2,4-difluorobenzyl)-N-(4-hydroxybenzyl)-2-methyl-3-nitroaniline

Product 1

HCID 68857423HCID 68857423, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

The product from Example 33A (0.1 g, 26 mmoles) in DMF (0.65 mL) was treated with sodium hydride (0.011 g, 0.26 mmoles). After 10 minutes, the reaction mixture was treated with cinnamyl bromide (0.10 g, 0.52 mmoles) and shaken overnight. The mixture was diluted with diethyl ether (50 mL), washed with saturated ammonium chloride (50 mL) and water (2×50 mL), brine (50 mL), dried (Na2SO4), filtered and the filtrate concentrated under reduced pressure to provide the title compound which was used in the next step without further purification.

Workup

  1. washwashed with saturated ammonium chloride (50 mL) and water (2×50 mL), brine (50 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-f23448d4367f412eb65a093861d52bb2
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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