Methylamine → 4-Bromo-N-methylbenzamide

HRID 2256064Notes

Reaction equation

HRID 2256064 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][NH2:12]>O1CCCC1.O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:12][CH3:11])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 1861134-Bromo-N-methylbenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromobenzoyl chloride (5.6 g) in 50 mL of tetrahydrofuran was cooled to 0° C. and treated with aqueous methylamine (5 mL of 40%). After the addition was complete, the reaction mixture was allowed to warm to room temperature and stirred for 16 hours. At the end of this period, the reaction mixture was diluted with water, extracted with ethyl acetate and the organic layer was washed with 10% HCl followed by sodium carbonate. Upon drying over magnesium sulfate and evaporation, a white solid was obtained (4.64 g); MS: 214; NMR: 3.0 (d, J=5, 3), 6.2 (br, 1), 7.5-7.6 (m, 2), 7.6-7.7 (m, 2).

Workup

  1. additionAfter the addition
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with 10% HCl
  4. dry with materialUpon drying over magnesium sulfate and evaporation
  5. customa white solid was obtained (4.64 g)

Sources & evidence

ORD record
ord-14c218b7fab14d8cade3402fa8132975
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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