Sodium hydride → 2-Bromo-N-(4-methoxy-benzyl)-N-(2-methyl-allyl)-5-nitro-benzamide

HRID 889948Notes

Reaction equation

HRID 889948 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:5]=1[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[O:7].Br[CH2:26][C:27]([CH3:29])=[CH2:28]>CN(C=O)C>[Br:3][C:4]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:5]=1[C:6]([N:8]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)[CH2:28][C:27]([CH3:29])=[CH2:26])=[O:7]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3577853-Bromo-2-methyl-1-propeneHCID 21959423N-(4-methoxybenzyl)-2-bromo-5-nitrobenzamide

Product 1

HCID 219593762-Bromo-N-(4-methoxy-benzyl)-N-(2-methyl-allyl)-5-nitro-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (1.22 g) in DMF (130 ml) was added 2-bromo-N-(4-methoxy-benzyl)-5-nitro-benzamide (6.2 g) in DMF (60 ml) at −78° C. The mixture was warmed to 0° C., 3-bromo-2-methyl-propene (4.57 g) was added and the mixture was stirred for 2 h at 0° C. The reaction was poured into ice water, extracted with EtOAc (2×400 ml), dried over MgSO4, filtered and concentrated to a DMF solution which was used without further purification.

Workup

  1. extractionextracted with EtOAc (2×400 ml)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to a DMF solution which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-f1449699dacd4621b2835c162719c7fd
Source dataset
uspto-grants-2006_02
Patent number
US06995162B2

Reaction notes

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