N-Methylacetamide → HCID 12839032, compound

HRID 1496852Notes

Reaction equation

HRID 1496852 reaction equation
[CH3:1][NH:2][C:3](=[O:5])[CH3:4].CC(C)([O-])C.[K+].[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1.C(OC(=O)C)C>C1COCC1.O>[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:2]([CH3:1])[C:3](=[O:5])[CH3:4])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 6582N-MethylacetamideHCID 8857Ethyl AcetateHCID 685274-Bromobenzyl bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 12839032HCID 12839032, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

1.316 g N-methylacetamide was dissolved in 60 mL THF. 2.02 g Potassium tert-butoxide was added and the mixture stirred for 20 min at 50° C. Then 3 g of 4-bromobenzylbromide dissolved in 10 mL THF was added and the mixture stirred for 2 h at 50° C. After cooling ethylacetate and water were added and the organic phase extracted with water (1×), dried and the solvent distilled off to yield 2.8 g N-(4-bromobenzyl)-N-methylacetamide as an oil.

Workup

  1. additionwas added
  2. stirringthe mixture stirred for 2 h at 50° C
  3. additionwere added
  4. extractionthe organic phase extracted with water (1×)
  5. customdried
  6. distillationthe solvent distilled off

Sources & evidence

ORD record
ord-56e1f18917de4d3e9cae9d7c1d948da0
Source dataset
uspto-grants-2015_12
Patent number
US09199937B2

Reaction notes

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