1-(Bromomethyl)-4-chlorobenzene → 2-(1H-1,2,3-Benzotriazol-1-yl)-3-(4-chlorophenyl)-N-methoxy-N-methyl-propanamide

HRID 30385

Reaction equation

HRID 30385 reaction equation
[N:1]1([CH2:10][C:11]([N:13]([O:15][CH3:16])[CH3:14])=[O:12])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=1>C1COCC1>[N:1]1([CH:10]([CH2:32][C:31]2[CH:34]=[CH:35][C:28]([Cl:27])=[CH:29][CH:30]=2)[C:11]([N:13]([O:15][CH3:16])[CH3:14])=[O:12])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 2733832Lithium HexamethyldisilazideHCID 222704902-(1H-1,2,3-benzotriazol-1-yl)-N-methoxy-N-methylacetamide

Product 1

HCID 222706332-(1H-1,2,3-Benzotriazol-1-yl)-3-(4-chlorophenyl)-N-methoxy-N-methyl-propanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.0 g (9 mmol) of 2-(1H-1,2,3-benzotriazol-1-yl)-N-methoxy-N-methylacetamide in 15 mL anhydrous THF at −78° C., 10 mL (10 mmol) of 1M lithium bis(trimethylsilyl)amide was added dropwise. After stirring for 25 min, a solution of 2.06 g (10 mmol) of 4-chlorobenzyl bromide in 2 mL anhydrous THF was added. The resulting reaction mixture was allowed to warm to RT and stirred for 6 h. This reaction was quenched, diluted with 75 mL EtOAc and washed 3 times with 10 mL each of brine, After drying the organic phase solvent removal afforded a crude product which was purified on silica gel using 40% EtOAc in hexane as solvent to afford the desired product as a solid. 1H NMR: (CDCl3): δ 3.2 (s, 3H), 3.34 (s, 3H), 3.52 (m, 1H), 3.7 (m, 1H), 6.32 (t, 1H), 6.9-8.2 (m, 8H).

Workup

  1. customThe resulting reaction mixture
  2. stirringstirred for 6 h
  3. customThis reaction was quenched
  4. additiondiluted with 75 mL EtOAc
  5. washwashed 3 times with 10 mL each of brine
  6. customAfter drying
  7. customthe organic phase solvent removal
  8. customafforded a crude product which
  9. customwas purified on silica gel using 40% EtOAc in hexane as solvent

Sources & evidence

ORD record
ord-5cd5b028df3246528087d6b0b126e15f
Source dataset
uspto-grants-2008_09
Patent number
US07423067B2

Linked notes

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